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

HRID 269995
Notes
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Reaction equation

HRID 269995 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-37021b198eff4adea582323388cd9a13
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07449477B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes