4-(4-tert-Butoxycarbonylpiperazinyl)phenylboronic acid, pinacol ester → 2-(Trimethylsilyl)ethyl 4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}isoquinoline-6-carboxylate

HRID 1959958Notes

Reaction equation

HRID 1959958 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.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][C:44](B3OC(C)(C)C(C)(C)O3)=[CH:43][CH:42]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][C:44]([C:7]3[C:16]4[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]=4)[CH:10]=[N:9][CH:8]=3)=[CH:43][CH:42]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 27955144-(4-tert-Butoxycarbonylpiperazinyl)phenylboronic acid, pinacol esterHCID 584957602-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate

Product 1

HCID 667455782-(Trimethylsilyl)ethyl 4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}isoquinoline-6-carboxylateYield 79.5%

Procedure

Using 2-(trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate (1.00 g, 2.38 mmol) and tert-butyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (998 mg, 2.57 mmol), the desired title compound (1.01 g, yield 79%) was obtained by the same method as in Example 4 (4a).

Sources & evidence

ORD record
ord-2aa86ff5e55d416fa8bc70ab4ffbdd7a
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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