4-Aminocarbonylphenylboronic acid → 1,1-dimethylethyl 7-[4-(amino-carbonyl)phenyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 70316Notes

Reaction equation

HRID 70316 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.[NH2:26][C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28]>>[NH2:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]3)=[CH:9][CH:8]=2)=[CH:31][CH:30]=1)=[O:28]

Participants

3

Reactant 2

HCID 27378114-Aminocarbonylphenylboronic acidHCID 21250582tert-butyl 7-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 582763631,1-dimethylethyl 7-[4-(amino-carbonyl)phenyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Procedure

The title compound was prepared from 1,1-dimethylethyl 7-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinoline carboxylate (Ex V-17) and 4-(aminocarbonyl)-phenyl boronic acid according to the procedure described for I-VII-9. Tan solid; LC/MS (method A) 2.62 min; m/z 353 (M+H, 75%), 297 ([M-C4H8]+H, 100%).

Workup

  1. customLC/MS (method A) 2.62 min

Sources & evidence

ORD record
ord-08c9944d32644cfc9e1cabe32a40c285
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

Loading…