Potassium Carbonate → HCID 67330532, compound

HRID 1672368Notes

Reaction equation

HRID 1672368 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([SH:20])[C:13]3[CH:14]=[CH:15][N:16]=[CH:17][C:18]=3[CH:19]=2)=[CH:6][CH:5]=1.[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29]Br)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29][S:20][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 67331618HCID 67331618, compound

Product 1

HCID 67330532HCID 67330532, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 7-(4-methoxy-phenyl)-isoquinoline-5-thiol sodium salt (0.29 g, 1 mmol) in acetone (10 mL), add (2-bromo-ethyl)-carbamic acid tert-butyl ester (0.22 g, 1 mmol) and potassium carbonate (0.14 g, 1 mmol). Stir the mixture at room temperature for 4 hr then load onto a silica gel column, and elute with 65% ethyl acetate in hexane to afford the title compound (0.35 g, 86%). Mass spectrum (LCMS) m/z=355.2 (M+H+).

Workup

  1. washelute with 65% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1d53139da907430bb66dc4fb24275843
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

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