HCID 11336372, compound → HCID 67486593, compound

HRID 1180245Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11](Br)=[CH:12][N:13]=[C:7]2[C:6]=1[F:15])=[O:4].[F:16][C:17]1[CH:18]=[C:19]([C:38]#[N:39])[C:20]([C:23]2[CH:28]=[C:27](B3OCC(C)(C)CO3)[CH:26]=[CH:25][C:24]=2[F:37])=[CH:21][CH:22]=1>>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:27]3[CH:26]=[CH:25][C:24]([F:37])=[C:23]([C:20]4[CH:21]=[CH:22][C:17]([F:16])=[CH:18][C:19]=4[C:38]#[N:39])[CH:28]=3)=[CH:12][N:13]=[C:7]2[C:6]=1[F:15])=[O:4]

Participants

Reactant 2

HCID 11336372HCID 11336372, compound

HCID 67486735HCID 67486735, compound

Product 1

HCID 67486593HCID 67486593, compoundYield 53%

Procedure

3-Bromo-8-fluoroimidazo[1,2-α]pyridine-7-carboxylic acid methyl ester (0.10 g, 0.37 mmol) and 4,2′-difluoro-5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)biphenyl-2-carbonitrile (0.15 g, 0.44 mmol) were coupled following the procedure in Example 1 to afford 3-(2′-cyano-2,4′-difluorobiphenyl-5-yl)-8-fluoroimidazo[1,2-α]pyridine-7-carboxylic acid methyl ester (79 mg, 53%) as a white solid: δH (400 MHz, CDCl3) 4.00 (3H, s), 7.35 (1H, dd, J 7 and 7), 7.34-7.46 (2H, m), 7.53-7.66 (4H, m), 7.85 (1H, s), 8.24 (1H, d, J 7); m/z (ES+) 408 (100%, [MH]+).

Sources & evidence

ORD record: ord-d486ae11a7aa4839abdd20d684dad26c
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279580B2

Reaction notes

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