Sodium Carbonate → HCID 86610755, compound

HRID 269995Notes

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]

Participants

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

temperatureAfter cooling to room temperature
filtrationfiltered
concentrationconcentrated
dissolutionThe residue is dissolved in EtOAc
washwashed with brine
dry with materialdried over Na2SO4
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

Loading…