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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Tri-tert-butylphosphine tetrafluoroborate → methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate

HRID 595119
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HRID 595119 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:22]=[CH:21][C:20]2[N:19]3[CH:23]=[CH:24][N:25]=[C:18]3[CH2:17][O:16][C:15]=2[C:14]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:11])=[O:10].[CH2:30]([N:32]([CH2:49][CH3:50])[CH2:33]/[CH:34]=[CH:35]\[Sn](CCCC)(CCCC)CCCC)[CH3:31].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.CS(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:30]([N:32]([CH2:49][CH3:50])[CH2:33]/[CH:34]=[CH:35]\[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:22]=[CH:21][C:20]2[N:19]3[CH:23]=[CH:24][N:25]=[C:18]3[CH2:17][O:16][C:15]=2[C:14]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:11])=[O:10])[CH3:31]
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참가 물질

7

반응물 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 70983693methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate2회HCID 86684726N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)amine2회

생성물 1

HCID 86712815methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate
수율 24.8%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 679Dimethyl Sulfoxide용매HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

A mixture of methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate (Intermediate 25, 0.598 g), N,N-diethyl-N—((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (Intermediate 3, 0.997 g), tris-(dibenzylideneacetone)dipalladium (0) (0.057 g) and tri-tert-butylphosphonium tetrafluoroborate (0.036 g) in dioxane (15 mL) and DMSO (1.5 mL) was de-gassed and purged with nitrogen then heated to 95° C. under an atmosphere of nitrogen for 2 hours. Further amounts of tris-(dibenzylideneacetone)dipalladium (0) (0.057 g) and tri-tert-butylphosphonium tetrafluoroborate (0.036 g) were added and the mixture stirred and heated at 95° C. for 2 hours. Further amounts of N,N-diethyl-N—((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (Intermediate 3, 0.997 g), tris-(dibenzylideneacetone)dipalladium (0) (0.057 g) and tri-tert-butylphosphonium tetrafluoroborate (0.036 g) were added and the mixture was stirred and heated at 95° C. for 30 minutes. After cooling, the mixture was diluted with ethyl acetate and washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-30% to give methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-5-oxa-3,9b-diaza-cyclopenta[a]naphthalene-6-carboxylate (0.158 g) as a light brown foam.

후처리

  1. customwas de-gassed
  2. custompurged with nitrogen
  3. additionFurther amounts of tris-(dibenzylideneacetone)dipalladium (0) (0.057 g) and tri-tert-butylphosphonium tetrafluoroborate (0.036 g) were added
  4. temperatureheated at 95° C. for 2 hours
  5. additionFurther amounts of N,N-diethyl-N—((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (Intermediate 3, 0.997 g), tris-(dibenzylideneacetone)dipalladium (0) (0.057 g) and tri-tert-butylphosphonium tetrafluoroborate (0.036 g) were added
  6. stirringthe mixture was stirred
  7. temperatureheated at 95° C. for 30 minutes
  8. temperatureAfter cooling
  9. additionthe mixture was diluted with ethyl acetate
  10. washwashed with water
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated in vacuo
  14. customthe residue was purified by chromatography on silica
  15. washeluting with a mixture of methanol and DCM with a gradient of 0-30%

출처 및 근거

ORD 기록
ord-6c5bf68b577f47cf86f1f1c2d7ef8556
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242997B2

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