Ethyl 2-(4-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylate → Ethyl 2-(2-amino-4-bromoanilino)benzo[b]thiophene-3-carboxylate

HRID 1281784Notes

Reaction equation

HRID 1281784 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([NH:6][C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([N+:23]([O-])=O)[CH:3]=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:23][C:4]1[CH:3]=[C:2]([Br:1])[CH:22]=[CH:21][C:5]=1[NH:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 18422146Ethyl 2-(4-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18422347Ethyl 2-(2-amino-4-bromoanilino)benzo[b]thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 19 and using ethyl 2-(4-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylate, ethyl acetate, 10% palladium-carbon and hydrogen (60 atm kg/cm2), ethyl 2-(2-amino-4-bromoanilino)benzo[b]thiophene-3-carboxylate is obtained.

Workup

  1. customMaterial Synthesis Example 19

Sources & evidence

ORD record
ord-7dfcc7c270da4ab69f698d98167c725d
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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