4-Nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide → 4-Amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide

HRID 1986654Notes

Reaction equation

HRID 1986654 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:8]([O:26][CH3:27])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:22]([N+:23]([O-])=O)[C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[C:8]([O:26][CH3:27])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:22]([NH2:23])[C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 117547814-Nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amideHCID 178418361HCID 178418361, compound

Product 1

HCID 100723074-Amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amideYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

The above nitro compound (200 mg, 0.42 mmol) was suspended in about 10 mL EtOAc and 10% Pd/C (50 mg) in 2 mL EtOAc was added. Hydrogen gas was introduced into the flask from an H2-filled balloon attached to a needle inserted through a septum. The black suspension was stirred 12 h at room temperature. After stirring 12, the black suspension was filtered through diatomaceous earth and the filter cake was washed several times with EtOAc. The combined filtrates were dried (MgSO4), filtered and the solvent was removed to afford 4-amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide as a pale yellow solid (170 mg, 90%).

Workup

  1. additionfilled balloon
  2. stirringAfter stirring 12
  3. filtrationthe black suspension was filtered through diatomaceous earth
  4. washthe filter cake was washed several times with EtOAc
  5. dry with materialThe combined filtrates were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-977ec2587c6f446dab9e21bac298e79e
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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