2-Fluoropyridine-4-boronic acid → 8-(2-Fluoro-pyridin-4-yl)-3-methyl-1-(2-methyl-2H-pyrazol-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445555Notes

Reaction equation

HRID 445555 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]1[CH:29]=[C:28](B(O)O)[CH:27]=[CH:26][N:25]=1>>[F:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:22])[C:13](=[O:21])[N:14]([C:15]5[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)[CH:27]=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 59620095HCID 59620095, compound2×

Product 1

HCID 498352528-(2-Fluoro-pyridin-4-yl)-3-methyl-1-(2-methyl-2H-pyrazol-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

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, 65 mg, 0.181 mmol) and 2-fluoropyridine-4-boronic acid (Frontier Scientific, Logan, USA, 33 mg, 0.236 mmol) to give the title compound as a pink solid. (HPLC: tR 2.55 min (Method A); M+H=375 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.08 (s, 1H), 8.35-8.26 (m, 1H), 8.22-8.13 (m, 1H), 8.10-8.01 (m, 1H), 7.84-7.76 (m, 1H), 7.43-7.35 (m, 1H), 7.29-7.23 (m, 1H), 7.23-7.16 (m, 1H), 6.73 (s, 1H), 3.68 (s, 3H), 3.60 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-f0c63c7fdb27495f885cbf7bcafdd129
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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