3-Pyridinylboronic acid → HCID 49835250, compound

HRID 445554Notes

Reaction equation

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

Participants

Reactant 2

HCID 27343783-Pyridinylboronic acid

HCID 59619981HCID 59619981, compound2×

Product 1

HCID 49835250HCID 49835250, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate H, 39 mg, 0.100 mmol) and 3-pyridineboronic acid (Aldrich, Buchs, Switzerland, 15 mg, 0.122 mmol) to give the title compound as an off-white foam. (HPLC: tR 2.08 min (Method A); M+H=385 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.00 (s, 1H), 8.70-8.64 (m, 1H), 8.60-8.55 (m, 1H), 8.16-8.10 (m, 1H), 7.99-7.92 (m, 1H), 7.90-7.84 (m, 1H), 7.54-7.47 (m, 2H), 3.82 (s, 3H), 3.60 (s, 3H), 2.09 (s, 3H), 1.92 (s, 3H))

Workup

customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record: ord-d28684a9fdd9476493190e7dac32607c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Reaction notes

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