3-(3-Bromo-2,6-difluorophenyl)pyridine → 7-(1,1-Difluoroethyl)-3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyrimidine

HRID 2183984Notes

Reaction equation

HRID 2183984 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([Sn](CCCC)(CCCC)CCCC)=[CH:12][N:13]=[C:7]2[N:6]=1)([F:4])[CH3:3].Br[C:28]1[C:29]([F:41])=[C:30]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)[C:31]([F:34])=[CH:32][CH:33]=1>>[F:4][C:2]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:32]3[CH:33]=[CH:28][C:29]([F:41])=[C:30]([C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)[C:31]=3[F:34])=[CH:12][N:13]=[C:7]2[N:6]=1)([F:1])[CH3:3]

Participants

3

Reactant 2

HCID 222400863-(3-Bromo-2,6-difluorophenyl)pyridineHCID 697094827-(1,1-Difluoroethyl)-3-tributylstannylimidazo[1,2-alpha]pyrimidine

Product 1

HCID 101338457-(1,1-Difluoroethyl)-3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyrimidine

Procedure

7-(1,1-Difluoroethyl)-3-tributylstannylimidazo[1,2-α]pyrimidine was reacted with 3-(3-bromo-2,6-difluorophenyl)pyridine following the procedure described in Example 32 to give 7-(1,1-difluoroethyl)-3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine as a white solid: δH (360 MHz, CDCl3) 2.16 (1H, t, J 19), 7.22-7.78 (1H, m), 7.31 (1H, d, J 7), 7.59 (1H, ddd, J 8, 3 and 1), 7.52-7.59 (1H, m), 7.85 (1H, dd, J 8 and 1), 8.03 (1H, s), 8.39 (1H, dd, J 7 and 3), 8.69 (1H, d, J 5 and 3), 8.78 (1H, s); m/z (ES+) 373 (M++H).

Sources & evidence

ORD record
ord-80f2c7c9175e47cdbfb0c9f4f1536c32
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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