HCID 17964842, compound → HCID 9982154, compound

HRID 1180321Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][C:18]=1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[S:39]([CH3:42])(=[O:41])=[O:40]>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[C:10]([F:11])[C:5]3=[N:4][CH:3]=2)=[CH:19][C:18]=1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[S:39]([CH3:42])(=[O:41])=[O:40]

Participants

Reactant 2

HCID 17964842HCID 17964842, compound

HCID 67487014HCID 67487014, compound

Product 1

HCID 9982154HCID 9982154, compoundYield 42%

Procedure

3-Bromo-8-fluoro-7-trifluoromethylimidazo[1,2-α]pyridine was coupled to 2-(2,4′-difluoro-2′-methanesulfonylbiphenyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as described in Example 1 to give 3-(2,4′-difluoro-2′-methanesulfonylbiphenyl-5-yl)-8-fluoro-7-trifluoromethylimidazo[1,2-α]pyridine as a white solid (147 mg, 42%): δH (400 MHz, CDCl3) 2.91 (3H, s), 6.99 (1H, dd, J 7 and 6), 7.35-7.47 (3H, m), 7.61-7.65 (2H, m), 7.85 (1H, s), 7.98-8.01 (1H, m), 8.48 (11H, d, J 7); m/z (ES+) 471 [MH+].

Sources & evidence

ORD record: ord-89846bd52beb400bbb91f50e8e84ce58
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279580B2

Reaction notes

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