4-Cyano-3-methoxyphenylboronic acid → HCID 178487651, compound

HRID 579063Notes

Reaction equation

HRID 579063 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:14])=[CH:11][N:10]=2)[C:6]=1[O:7]C.[C:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][C:28]=1[O:36][CH3:37])#[N:26]>>[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:3]=[N:4][N:5]([C:9]3[CH:24]=[CH:23][C:12]([C:13]([NH:15][CH2:16][CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:14])=[CH:11][N:10]=3)[C:6]=2[OH:7])=[CH:29][C:28]=1[O:36][CH3:37])#[N:26]

Participants

3

Reactant 2

HCID 450912364-Cyano-3-methoxyphenylboronic acidHCID 1176002516-(4-bromo-5-methoxy-1H-pyrazol-1-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide

Product 1

HCID 178487651HCID 178487651, compound

Procedure

The title compound was prepared in a manner similar to Example 213 using 6-(4-bromo-5-methoxy-1H-pyrazol-1-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide (50 mg, 0.127 mmol), (4-cyano-3-methoxyphenyl)boronic acid. 1H NMR (400 MHz, DMSO-d6) δ 1.14 (d, J=10.6 Hz, 2 H) 1.55 (d, J=11.9 Hz, 3 H) 3.11 (br. s., 2 H) 3.72-3.90 (m, 7 H) 6.47 (s, 1 H) 7.41 (d, J=15.4 Hz, 3 H) 7.77 (br. s., 1 H) 8.03-8.23 (m, 3 H) 8.41-8.60 (m, 2 H) 8.77 (br. s., 1 H). MS m/z [M+H]+ 434.4.

Sources & evidence

ORD record
ord-716b5e72d0914ff1a50674dea9669984
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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