6-Chloro-3-pyridinecarbonitrile → HCID 9943829, compound

HRID 1796014Notes

Reaction equation

HRID 1796014 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:15]1[N:19]2[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[N:23][C:18]2=[N:17][CH:16]=1)CCC>>[F:26][C:24]([F:25])([F:27])[C:22]1[CH:21]=[CH:20][N:19]2[C:15]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=3)=[CH:16][N:17]=[C:18]2[N:23]=1

Participants

3

Reactant 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9943829HCID 9943829, compoundYield 35.1%

Procedure

6-Chloronicotinonitrile (295 mg, 2.13 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.4 mmol) by the method of Example 1 to give 6-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)nicotinonitrile (142 mg) as a white solid: δH (400 MHz, DMSO) 7.79 (1H, d, J 7), 8.35 (1H, m), 8.43 (1H, m), 9.06 (1H, s), 9.14 (1H, s), 10.41 (1H, d, J 7); m/z (ES+) 290 (M++H).

Sources & evidence

ORD record
ord-3dee11aeab484b298130a01e2c08a085
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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