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Cesium carbonate → methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-vinylbenzoate

HRID 595108
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HRID 595108 반응식
[C:1]([O:5][C:6]([N:8]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13](OS(C(F)(F)F)(=O)=O)[C:12]([C:27]2[N:28]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[N:29]=[CH:30][CH:31]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:45](B1OC(C)(C)C(C)(C)O1)=[CH2:46].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:41]([O:40][C:38]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH:45]=[CH2:46])[C:12]([C:27]2[N:28]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[N:29]=[CH:30][CH:31]=2)=[CH:11][CH:10]=1)=[O:39])([CH3:43])([CH3:44])[CH3:42]
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86712819methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-trifluoromethanesulfonyloxybenzoate2회

생성물 1

HCID 86712818methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-vinylbenzoate

시약·촉매·용매 3

HCID 178419050
HCID 178419050, 화합물
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-trifluoromethanesulfonyloxybenzoate (Intermediate 11, 4.35 g), vinylboronic acid pinacol ester (1.9 mL), bis(triphenylphosphine)palladium (II) dichloride (0.255 g) and cesium carbonate (7.1 g) in dioxane (300 mL) and water (47 mL) was de-gassed and purged with nitrogen. The mixture was then heated to 80° C. for 4 hours. After cooling, the mixture was diluted with ether and the organic layer was separated, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-vinylbenzoate (2.84 g) as a gum.

후처리

  1. customwas de-gassed
  2. custompurged with nitrogen
  3. temperatureAfter cooling
  4. additionthe mixture was diluted with ether
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

출처 및 근거

ORD 기록
ord-f0bbfa1577ad412a98829974b58e469a
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242997B2

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