6-Bromo-2,3'-bipyridine → 6-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidin-3-yl]-2,3'-bipyridine

HRID 1796104Notes

Reaction equation

HRID 1796104 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][N:10]3[C:13]([Sn](CCCC)(CCCC)CCCC)=[CH:14][N:15]=[C:9]3[N:8]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Br[C:30]1[N:35]=[C:34]([C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)[CH:33]=[CH:32][CH:31]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][N:10]3[C:13]([C:30]4[N:35]=[C:34]([C:36]5[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=5)[CH:33]=[CH:32][CH:31]=4)=[CH:14][N:15]=[C:9]3[N:8]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 135464546-Bromo-2,3'-bipyridineHCID 695607597-([1,2,4]Triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-alpha]pyrimidine

Product 1

HCID 102695336-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidin-3-yl]-2,3'-bipyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To the degassed solution of 7-([1,2,4]triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-α]pyrimidine was added 6-bromo-2,3′-bipyridine (prepared according to Example 49) (0.39 g, 1.65 mmol) and tetrakis(triphenylphosphine)palladium(0) (173 mg, 0.10 mmol) and the mixture heated at reflux for 3 h. The crude reaction was adsorbed onto silica and purified by chromatography on silica gel eluting with a dichloromethane, methanol, aqueous ammonia (33%) mixture in the volume ratios of 90:5:0.5 respectively to give 6-[7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]-2,3′-bipyridine as a hygroscopic solid following crystallisation from dichloromethane/ethyl acetate. Addition of an excess of 1M HCl in ether to a solution of the product in a methanol/ether solvent mixture gave 50 mg of the dihydrochloride salt as a white solid: δH (360 MHz, CDCl3) 5.62 (2H, s), 6.96 (1H, d, J 7), 7.47 (1H, dd, J 4.7 and 4.7), 7.66 (1H, d, J 7.7), 7.78 (1H, d, J 7.9), 7.91 (1H, t, J 9), 8.05 (1H, s), 8.23-8.27 (1H, m), 8.36 (1H, s), 8.41 (1H, s), 8.71-8.72 (1H, m), 9.25 (1H, s), 10.30 (1H, d, J 7.2); m/z (ES+) 355 (M++H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. customThe crude reaction
  4. custompurified by chromatography on silica gel eluting with a dichloromethane, methanol, aqueous ammonia (33%) mixture in the volume ratios of 90:5:0.5 respectively

Sources & evidence

ORD record
ord-a6ea1cf2589740f0bbc75d0d586755ff
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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