2-Bromo-6-phenylpyridine → HCID 10268818, compound

HRID 1796070Notes

Reaction equation

HRID 1796070 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[N:23]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[N:27][C:22]2=[N:21][CH:20]=1)CCC>>[C:8]1([C:4]2[N:3]=[C:2]([C:19]3[N:23]4[CH:24]=[CH:25][C:26]([C:28]([F:29])([F:30])[F:31])=[N:27][C:22]4=[N:21][CH:20]=3)[CH:7]=[CH:6][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 5686792-Bromo-6-phenylpyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 10268818HCID 10268818, compoundYield 34.4%

Procedure

2-Bromo-6-phenylpyridine (0.17 g, 0.7 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.9 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-10%) and trituration with ethyl acetate gave 3-(6-phenylpyridin-2-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (82 mg) as a pale yellow solid: δH (400 MHz, CDCl3) 7.39 (1H, d, J 7), 7.53 (3H, m), 7.70 (1H, d, J 8), 7.78 (1H, d, J 8), 7.91 (1H, dd, J 8 and 8), 8.01 (2H, d, J 8), 8.53 (1H, s), 10.62 (1H, d, J 7); m/z (ES+) 341 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-10%) and trituration with ethyl acetate

Sources & evidence

ORD record
ord-48a6f501ae2648aebb3bf98fde8b693f
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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