4-Chloro-1H-pyrrolo[2,3-b]pyridine → 4-(4-Phenyl-1H-imidazol-1-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 44911Notes

Reaction equation

HRID 44911 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[C:11]1([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([C:17]2[N:18]=[CH:19][N:20]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[NH:8][CH:9]=[CH:10][C:3]=34)[CH:21]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 178418822HCID 178418822, compound

Product 1

HCID 177544094-(4-Phenyl-1H-imidazol-1-yl)-1H-pyrrolo[2,3-b]pyridineYield 291%

Procedure

A melt of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.00033 mol) in 4-phenyl-1H-imidazole (0.24 g, 0.0016 mol) was heated at 200° C. overnight. The reaction was partitioned between ethyl acetate and saturated NaHCO3, separated and the organic phase was washed with brine. The organic layer was then dried and evaporated to give 250 mg of an orange oil. The oil was chromatographed with 7% MeOH/DCM, 0.7% NH4OH, sample in solvent system. Collected 74 mg of the product as an orange glass. The glass was triturated with hot DCE (1.5 mL) to give 51 mg of a brown solid which was dried at 60° C. for 4 h to afford the desired product (50 mg, 59 yield).

Workup

  1. customThe reaction was partitioned between ethyl acetate and saturated NaHCO3
  2. customseparated
  3. washthe organic phase was washed with brine
  4. customThe organic layer was then dried
  5. customevaporated

Sources & evidence

ORD record
ord-cc5b571a639f460aa3e9f3cd8491c27f
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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