tert-Butyldimethylsilyl chloride → HCID 88959644, compound

HRID 2178718Notes

Reaction equation

HRID 2178718 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>>[Si:13]([O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Cl:1])=[N:3][CH:4]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 42818821-Chloro-4-hydroxyisoquinoline

Product 1

HCID 88959644HCID 88959644, compound

Procedure

1-Chloroisoquinolin-4-ol was treated with tert-butyldimethylsilyl chloride to produce 4-{[tert-butyl(dimethyl)silyl]oxy}-1-chloroisoquinoline. Halogen exchange gave 4-{[tert-butyl(dimethyl)silyl]oxy}-1-iodoisoquinoline, which was treated with copper iodide and methyl difluoro(fluorosulfonyl)acetate to produce 1-(trifluoromethyl)isoquinolin-4-ol.

Sources & evidence

ORD record
ord-516178d10cf1454b9c0266623d7deeb3
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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