2-Bromothiophene → HCID 22285443, compound

HRID 1062440Notes

Reaction equation

HRID 1062440 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Li]CCCC.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:20]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[C:21]([CH2:33][CH3:34])=[C:22]([C:24](N2CCC(=O)CC2)=[O:25])[N:23]=1>C1COCC1.CCCCCC>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:20]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[C:21]([CH2:33][CH3:34])=[C:22]([C:24]([C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)=[O:25])[N:23]=1

Participants

6

Reactant 3

HCID 138512-BromothiopheneHCID 22285623HCID 22285623, compoundHCID 178418339Butyllithium

Product 1

HCID 22285443HCID 22285443, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 2-bromothiophene (0.22 g, 1.36 mmol) in 2 mL THF was added 0.84 mL of a 1.6 M solution of BuLi in hexane under argon at −78° C. with stirring. The stirring was continued for 1 h. To this was added a solution of 1-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazol-4-yl]carbonyl}-4-piperidinone in 2 mL THF. The resultant mixture was stirred and gradually allowed to warm up to rt overnight. The reaction was quenched with saturated aqueous NH4Cl and the mixture was extracted with ethyl acetate. The organic layer was concentrated and the crude product was purified by HPLC to yield [2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazol-4-yl](2-thienyl)-methanone as a solid (60 mg, 31%): Rf=0.13 (1:5 ethyl acetate/hexanes).

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe crude product was purified by HPLC

Sources & evidence

ORD record
ord-c6eab549d7b449978004d5ec281c168c
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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