Ethyl Acetate → methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1442543

Reaction equation

HRID 1442543 reaction equation
Br[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[NH2:34])O1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 58679076methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (7 g, 20 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine (4.8 g, 22 mmol), sodium hydrogen carbonate (6.7 g, 80 mmol) and tetrakis(triphenylphosphine)palladium (230 mg, 0.2 mmol) in water (20 ml) and ethylene glycol dimethyl ether (50 ml) was stirred with heating under reflux for 4 hr. The reaction mixture was cooled to room temperature and ethyl acetate (200 ml) was added. The mixture was washed successively with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml) and saturated brine (100 ml), and dried over magnesium sulfate. Filtration and concentration under reduced pressure gave a crude product of methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate. The obtained compound was used for Step 10 without purification.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. washThe mixture was washed successively with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml) and saturated brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-5213c83512804d9ab0e83f5e35b2c222
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Linked notes

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