Tetrahydrofuran → 4-(1-(4-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-1H-pyrrol-2-yl)-3-methylbenzamide

HRID 238408Notes

Reaction equation

HRID 238408 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[O:29][CH3:30])[CH:12]=[CH:13][C:14]=2/C=C/C(OCC)=O)=[C:6]([CH3:31])[CH:5]=1)(=[O:3])[NH2:2].[H][H].C1C[O:37][CH2:36]C1>[Ni]>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:11]2[CH:12]=[CH:13][C:14]([CH2:36][OH:37])=[C:10]2[C:7]2[CH:8]=[CH:9][C:4]([C:1]([NH2:2])=[O:3])=[CH:5][C:6]=2[CH3:31])=[C:23]([O:29][CH3:30])[CH:24]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 86654217(E)-ethyl 3-(2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrol-3-yl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 671752774-(1-(4-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-1H-pyrrol-2-yl)-3-methylbenzamide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of (E)-ethyl 3-(2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrol-3-yl)acrylate (610 mg, 1.4 mmol) in THF (10 mL) was added Raney Ni (100 mg), and the reaction mixture was hydrogenated at room temperature under 1 atm of hydrogen for two hours. The reaction mixture was filtered, and the filtrate was concentrated to give the title compound (610 mg), which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f42ab8d736e248a3b6c55c106e5e5c72
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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