2-Bromo-6-(methoxymethyl)pyridine → HCID 9836225, compound

HRID 1796088Notes

Reaction equation

HRID 1796088 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][CH3:10])[N:3]=1.C([Sn](CCCC)(CCCC)[C:16]1[N:20]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[N:24][C:19]2=[N:18][CH:17]=1)CCC>>[CH3:10][O:9][CH2:8][C:4]1[N:3]=[C:2]([C:16]2[N:20]3[CH:21]=[CH:22][C:23]([C:25]([F:26])([F:27])[F:28])=[N:24][C:19]3=[N:18][CH:17]=2)[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 109435402-Bromo-6-(methoxymethyl)pyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9836225HCID 9836225, compoundYield 3.6%

Procedure

2-Bromo-6-methoxymethylpyridine (0.27 g, 1.34 mmol; prepared according to Shawcross et al. in J. Heterocyclic Chem., 1993, 33(2), 563-565) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.34 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-100%) and trituration with isohexane gave 3-(6-methoxymethylpyridin-2-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (15 mg) as a yellow solid: δH (400 MHz, CDCl) 3.54 (3H, s), 4.68 (2H, s), 7.34 (1H, d, J 7), 7.39 (1H, d, J 7), 7.73 (1H, d, J 7), 7.84 (1H, t, J 7), 8.52 (1H, s), 10.51 (1H, d, J 7); m/z (ES+) 309 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-100%) and trituration with isohexane

Sources & evidence

ORD record
ord-e758235b70cb4c44beb69359c54d4dde
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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