2-(Trifluoromethyl)pyridine-5-boronic Acid → HCID 49835249, compound

HRID 445552Notes

Reaction equation

HRID 445552 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:22])[C:13](=[O:21])[N:14]([C:15]4[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1>>[CH3:22][N:12]1[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:2]([C:28]4[CH:27]=[N:26][C:25]([C:24]([F:35])([F:34])[F:23])=[CH:30][CH:29]=4)=[CH:3][C:4]=3[C:5]=2[N:14]([C:15]2[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=2)[C:13]1=[O:21]

Participants

3

Reactant 2

HCID 251342782-(Trifluoromethyl)pyridine-5-boronic AcidHCID 59620095HCID 59620095, compound2×

Product 1

HCID 49835249HCID 49835249, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-1-(2-methyl-2H-pyrazol-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate E, 58 mg, 0.163 mmol) and 2-trifluoromethylpyridine-5-boronic acid (Frontier Scientific, Logan, USA, 40.5 mg, 0.212 mmol) to give the title compound as a red solid. (HPLC: tR 2.87 min (Method A); M+H=425 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.08 (s, 1H), 8.82 (d, 1H), 8.27-8.16 (m, 2H), 8.10-7.98 (m, 2H), 7.82 (d, 1H), 7.18-7.16 (m, 1H), 6.72 (s, 1H), 3.72 (s, 3H), 3.63 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-aadc4502323c4db4bbb7ffeb4368cc78
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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