HCID 17964829, compound → HCID 10341330, compound

HRID 1180283Notes

Reaction equation

HRID 1180283 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].CC1(C)COB([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][C:31]=2[F:38])OC1>>[F:38][C:31]1[CH:32]=[C:33]([C:34]#[N:35])[CH:36]=[CH:37][C:30]=1[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 17964829HCID 17964829, compoundHCID 674866802-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

Product 1

HCID 10341330HCID 10341330, compoundYield 9%

Procedure

2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and 4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-3-fluorobenzonitrile were coupled in the same way as in Example 30 to give 2,2′-difluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-4-carbonitrile as an off-white solid (9 mg, 9%): δH (400 MHz, d6-DMSO) 1.56 (6H, s), 7.27 (1H, t, J 7), 7.60 (1H, t, J 9), 7.81-7.92 (5H, m), 8.05 (1H, d, J 10), 8.47 (1H, d, J 7); m/z (ES+) 408 [MH+].

Sources & evidence

ORD record
ord-3eae8cd008934876aa0c4d14cc70c167
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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