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Cesium fluoride → ethyl 3-(3-hydroxypropyl)-7-(2-methoxyphenyl)-1H-indole-2-carboxylate

HRID 2199714
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HRID 2199714 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][OH:19].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+]>C1COCC1.C(OCC)(=O)C.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]>[OH:19][CH2:18][CH2:17][CH2:16][C:7]1[C:6]2[C:10](=[C:2]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH3:20])[CH:3]=[CH:4][CH:5]=2)[NH:9][C:8]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 25953Cesium fluorideHCID 27339582-Methoxyphenylboronic acidHCID 44558591Tri-t-butylphosphine fluoroborateHCID 68943187ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate

생성물 1

HCID 68940496ethyl 3-(3-hydroxypropyl)-7-(2-methoxyphenyl)-1H-indole-2-carboxylate

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of EXAMPLE 1B (456 mg) and 2-methoxyphenylboronic acid (182.4 mg) in THF (10 mL), tris(dibenzylideneacetone)dipalladium(0) (46 mg), tri-tert-butylphosphine tetrafluoroborate (15 mg) and CsF (456 mg) was stirred at ambient temperature, diluted with ethyl acetate (200 mL), washed with water and brine, and dried (Na2SO4), filtered and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate in hexanes.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-453d3d5134ad4186a962777432804195
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359296B2

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