2-Methylpyridine-5-boronic acid → HCID 49835247, compound

HRID 445551Notes

Reaction equation

HRID 445551 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[N:16]([CH3:21])[N:17]=[C:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH3:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1>>[CH3:21][N:16]1[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:28]5[CH:27]=[N:26][C:25]([CH3:24])=[CH:30][CH:29]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])=[CH:19][C:18]([CH3:20])=[N:17]1

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 59619709HCID 59619709, compound2×

Product 1

HCID 49835247HCID 49835247, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(2,5-dimethyl-2H-pyrazol-3-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate C, 50 mg, 0.135 mmol) and 2-methylpyridine-5-boronic acid (Frontier Scientific, Logan, USA, 28 mg, 0.181 mmol) to give the title compound as a red solid. (HPLC: tR 2.20 min (Method A); M+H=385 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.02 (s, 1H), 8.62-8.52 (m, 1H), 8.17-8.08 (m, 1H), 8.00-7.91 (m, 1H), 7.81-7.73 (m, 1H), 7.39-7.32 (m, 1H), 7.13 (s, 1H), 6.52 (s, 1H), 3.62 (s, 3H), 3.51 (s, 3H), 2.55-2.45 (3H), 2.29 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-beaa3d60dd8c4f498b3243968b4bc765
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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