Phenylboronic Acid → 2-(2-Methylphenyl)-5-[(5-phenylpyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one

HRID 341101Notes

Reaction equation

HRID 341101 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20](=[O:21])[C:11]2=[CH:12][NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1.Br[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]2[NH:31][C:32]3[C:33](F)=CC=C(F)[C:37]=3[C:38]3C=2C(=O)N(C2C=CC=CC=2F)N=3)=[C:25](F)[CH:24]=1.C1(B(O)O)C=CC=CC=1.C(N1C=C(B2OC(C)(C)C(C)(C)O2)C=N1)C(C)C>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20](=[O:21])[C:11]2=[CH:12][N:13]([CH2:33][C:32]3[CH:37]=[CH:38][C:29]([C:26]4[CH:25]=[CH:24][CH:23]=[CH:28][CH:27]=4)=[CH:30][N:31]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1

Participants

5

Reactant 4

HCID 66827Phenylboronic AcidHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 178424334HCID 178424334, compoundHCID 178514861HCID 178514861, compound

Product 1

HCID 699351882-(2-Methylphenyl)-5-[(5-phenylpyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one

Procedure

Using the procedure described in Example 95, substituting 5-[5-bromopyridin-2-yl)methyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one for 5-[(4-bromo-2-fluorophenyl)methyl-6,9-difluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one, and, substituting phenylboronic acid for 1-iso-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, the titled compound was obtained: 1H-NMR (400 MHz, CD3OD) δ 9.03 (1H, s), 8.77 (1H, s), 8.36-8.33 (1H, m), 8.10-8.07 (1H, m), 7.85 (1H, d, J=8.8 Hz), 7.68-7.37 (12H, m), 5.93 (2H, s), 2.29 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 442.9 [(M+H)+; calculated for C29H22N4O: 443.2].

Sources & evidence

ORD record
ord-86b514980dd94382854ce9520268056d
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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