Dimethylformamide → HCID 18476108, compound

HRID 1384406Notes

Reaction equation

HRID 1384406 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]3[C:14]([CH:18]=2)=[N:15][O:16][N:17]=3)[CH:5]=[C:6](OC)[CH:7]=1.C[Sn](C)(C)[C:21]1[CH:22]=[CH:23][C:24]2[N:25]([CH:27]=[CH:28][N:29]=2)[CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:53]=[O:54]>>[CH3:53][O:54][C:3]1[CH:2]=[CH:7][C:6]([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([CH:27]=[CH:28][N:29]=3)[CH:26]=2)=[CH:5][C:4]=1[C:10]1[CH:11]=[CH:12][C:13]2[C:14]([CH:18]=1)=[N:15][O:16][N:17]=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 18476099HCID 18476099, compoundHCID 18476121HCID 18476121, compound

Product 1

HCID 18476108HCID 18476108, compound

Conditions

Temperature
125 °C

Procedure

A stirred mixture of 5-(3-bromo-5-methoxyphenyl)benzofurazan (2.44 g, 8 mmol), 6-(trimethylstannyl) imidazol[1,2-a]pyridine (2.2 g, 7.9 mmol), triphenylphosphine (336 mg, 1.28 mmol), and bis(dibenzylidineacetone)palladium(0) (186 mg, 0.32 mmol) in dimethylformamide (60 mL) is heated at 125° C. under an argon atmosphere for 36 h. The solvent is evaporated off under reduced pressure to yield a crude product which is purified by chromatography (silica gel, 95% ethyl acetate/4.5% ethanol/0.5% aqueous NH3 (25%)) and recrystallised from ethyl acetate-t-butylmethyl ether to give 6-[4-methoxy-3-(5-benzofurazanyl)phenyl]imidazo[1,2-a]pyridine as a pale-yellow crystalline solid, m.p. 190-196° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customto yield a crude product which
  3. customis purified by chromatography (silica gel, 95% ethyl acetate/4.5% ethanol/0.5% aqueous NH3 (25%))
  4. customrecrystallised from ethyl acetate-t-butylmethyl ether

Sources & evidence

ORD record
ord-4109d98e5fcb4d958c8b834e7369f7e0
Source dataset
uspto-grants-2001_07
Patent number
US06258843B1

Reaction notes

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