4-Aminocarbonylphenylboronic acid → HCID 178451613, compound

HRID 2383482Notes

Reaction equation

Br[C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1.[C:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])[NH2:23]>>[C:22]([C:25]1[CH:26]=[C:27]([C:2]2[C:14]3[C:13]4[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=4[CH:7]=[N:6][C:5]=3[NH:4][N:3]=2)[CH:28]=[CH:29][CH:30]=1)(=[O:24])[NH2:23]

Participants

Reactant 2

HCID 27378114-Aminocarbonylphenylboronic acid

HCID 178451611HCID 178451611, compound

Product 1

HCID 178451613HCID 178451613, compound

Procedure

The compound, tert-butyl 1-(3-carbamoylphenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate was prepared using tert-butyl 1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate and 4-carbamoylphenylboronic acid as described in step-1 of general procedure U. The compound was obtained as a white solid (0.070 g, 39%); 1H NMR (400 MHz, DMSO-d6) δ13.98 (s, 1H), 8.40 (s, 1H), 8.13 (s, 1H), 8.08 (s, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.58 (m, 1H), 7.45 (s, 1H), 4.65 (s, 2H), 3.49 (m, 2H), 2.82 (m, 2H), 1.43 (s, 9H); LC-Mass [M+H]: 394.

Sources & evidence

ORD record: ord-3aadd9ffb2684fa2ac382fe6353ac27e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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