Potassium Carbonate → 6-Bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)isoquinolin-1(2H)-one

HRID 906399Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([CH3:32])([CH3:31])[CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:20][C:21]([CH3:32])([CH3:31])[CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 6-bromoisoquinolin-1(2H)-one (Example 1b, 1.5 g) dissolved in NMP (15 mL) was treated with potassium carbonate (1.48 g) and (3-bromo-2,2-dimethylpropoxy)(tert-butyl)dimethylsilane (2.26 g) under nitrogen. The resulting mixture was stirred at 70° C. for 10 h (low conversion), heating was continued at 100° C. for 10 h. The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (300 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography, elution with 20% diethyl ether in isohexane) to afford the subtitle compound (1.30 g) as an oil.

Workup

temperatureheating
waitwas continued at 100° C. for 10 h
extractionextracted with ethyl acetate (300 mL)
dry with materialThe organic was dried (MgSO4)
filtrationfiltered
customevaporated
customto afford crude product
customThe crude product was purified
wash(SiO2 chromatography, elution with 20% diethyl ether in isohexane)

Sources & evidence

ORD record: ord-6bc7604d7bfc462687ef4d6b742589fa
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012980B2

Reaction notes

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