4-Chlorophenylboronic acid → 2-(Trimethylsilyl)ethyl 4-(4-chlorophenyl)isoquinoline-6-carboxylate

HRID 1959951Notes

Reaction equation

HRID 1959951 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH:15]=2)[CH:10]=[N:9][CH:8]=1)(=O)=O.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH:15]=3)[CH:10]=[N:9][CH:8]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 584957602-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate

Product 1

HCID 667305822-(Trimethylsilyl)ethyl 4-(4-chlorophenyl)isoquinoline-6-carboxylateYield 71.5%

Procedure

From 2-(trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate (6.00 g, 14.2 mmol) and 4-chlorophenylboronic acid (3.30 g, 30.0 mmol), 2-(trimethylsilyl)ethyl 4-(4-chlorophenyl)isoquinoline-6-carboxylate (3.90 g, yield 71%) was obtained by the same method as in Example 8 (8a). Further, using this compound (3.90 g, 9.9 mmol), the desired title compound (1.96 g, yield 70%) was obtained by the same method as in Example 4 (4b).

Sources & evidence

ORD record
ord-7928105267804757832b92778afc8955
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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