Benzophenone imine → 1-Benzothiophen-6-amine

HRID 1986195Notes

Reaction equation

HRID 1986195 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.C(=[NH:24])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[S:7]1[CH:8]=[CH:9][C:5]2[CH:4]=[CH:3][C:2]([NH2:24])=[CH:10][C:6]1=2

Participants

6

Reactant 3

HCID 136809Benzophenone imineHCID 127444006-Bromo-benzo[b]thiopheneHCID 23676156Sodium t-butoxide

Product 1

HCID 2205911-Benzothiophen-6-amineYield 13.4%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

A mixture of 6-bromobenzo[b]thiophene (16.0 g, 76.0 mmol), benzophenone imine (16.6 g, 91.5 mmol), tris(dibenzylidineacetone)palladium(0) (0.72 g, 0.80 mmol), 1,1′-bis(diphenylphosphino)ferrocene (1.3 g, 2.3 mmol) and sodium tert-butoxide (10.8 g, 112 mmol) in toluene is refluxed for 20 hours. The solvent is evaporated and the residue is chromatographed on silica, eluting with dichloromethane) to give the title compound (1.52 g, 11% yield).

Workup

  1. temperatureis refluxed for 20 hours
  2. customThe solvent is evaporated
  3. customthe residue is chromatographed on silica
  4. washeluting with dichloromethane)

Sources & evidence

ORD record
ord-846b5a2f38f341c0b0446fa2af0c7b8b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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