Water → HCID 58679084, compound

HRID 1442549Notes

Reaction equation

HRID 1442549 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.[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31](B2OC(C)(C)C(C)(C)O2)=[C:32]([NH2:34])[CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.C(=O)([O-])O.[Na+]>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:32]1[CH:33]=[C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:29]=[CH:30][C:31]=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

7

Reactant 4

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 23152811HCID 23152811, compoundHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 58679084HCID 58679084, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (4.73 g, 13.8 mmol) and 5-benzyloxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine (5.84 g, 17.9 mmol) produced by the method described in WO2005/080399 in 1,2-dimethoxyethane (50 ml) and water (50 ml) were added sodium hydrogen carbonate (1.72 g, 20.7 mol) and tetrakis(triphenylphosphine)palladium (799 mg, 0.691 mol), and the mixture was stirred overnight with heating at 110° C. The reaction mixture was allowed to cool to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure and the residue was purified y silica gel column chromatography (hexane:ethyl acetate=3:1) to give methyl 5-(2-amino-4-benzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (5.93 g, yield 93%).

Workup

  1. customproduced by the method
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified y silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-da678a4396d04376adbbf6d5f3a14037
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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