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Sodium Carbonate → 7-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester

HRID 269995
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인쇄 미리보기

반응식

HRID 269995 반응식
[C:1]([O:5][C:6](=[O:8])[NH2:7])([CH3:4])([CH3:3])[CH3:2].[NH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]=2[CH:23]=[C:24](Br)[CH:25]=1)(=[O:15])=[O:14].[C:27]1(B2OCCCO2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CO.CCOC(C)=O>[C:1]([O:5][C:6](=[O:8])[NH2:7])([CH3:4])([CH3:3])[CH3:2].[NH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]=2[CH:23]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=1)(=[O:15])=[O:14]
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 642685Phenylboronic acid 1,3-propanediol esterHCID 866107567-Bromo-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester

생성물 1

HCID 866107557-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester수율 97%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 7-bromo-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester (1.50 g, 3.49 mmol), 2-phenyl-1,3,2-dioxaborinane (1.129 g, 6.98 mmol), Pd(dppb)Cl2 (211 mg, 0.0349 mmol) and Na2CO3 (2.0M, 12 mL) in ethylene glycol dimethyl ether (60 mL) and CH3OH (15 mL) is heated to 80° C. (oil bath) with stirring overnight. After cooling to room temperature, the mixture is diluted with EtOAc, filtered and concentrated. The residue is dissolved in EtOAc, washed with brine and dried over Na2SO4. The crude material is chromatographed on silica gel (gradient 50% EtOAc in hexane) to give 1.45 g (97% yield) 7-phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe crude material is chromatographed on silica gel (gradient 50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-37021b198eff4adea582323388cd9a13
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449477B2

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