Ethyl 3-ethynyl-6-nitro-1-benzothiophene-2-carboxylate → Ethyl 6-amino-3-ethyl-1-benzothiophene-2-carboxylate

HRID 1425268Notes

Reaction equation

HRID 1425268 reaction equation
[C:1]([C:3]1[C:7]2[CH:8]=[CH:9][C:10]([N+:12]([O-])=O)=[CH:11][C:6]=2[S:5][C:4]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[CH:2].[H][H]>CO.C1COCC1.[C].[Pd]>[NH2:12][C:10]1[CH:9]=[CH:8][C:7]2[C:3]([CH2:1][CH3:2])=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:5][C:6]=2[CH:11]=1

Participants

6

Reactant 2

HCID 86648747Ethyl 3-ethynyl-6-nitro-1-benzothiophene-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67549339Ethyl 6-amino-3-ethyl-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-ethynyl-6-nitro-1-benzothiophene-2-carboxylate obtained in Example (183d) was dissolved in methanol (16 mL) and THF (24 ml). A 10% palladium-carbon catalyst (120 mg) was added, and the mixture was stirred in a hydrogen atmosphere throughout the day. The reaction solution was filtered through celite and then concentrated under reduced pressure to obtain the title compound. The resulting compound was used for the next reaction without purification.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77ebf83e568148859ca0c3deb5d1cfeb
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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