Triethylamine → methyl 6-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1442545Notes

Reaction equation

HRID 1442545 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.C(N(CC)CC)C.[CH3:27][C:28]1([CH3:35])[C:32]([CH3:34])([CH3:33])[O:31][BH:30][O:29]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Cl-].[NH4+]>O1CCOCC1>[CH:14]1([C:3]2[C:4]3[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:5]=3[NH:6][C:2]=2[B:30]2[O:31][C:32]([CH3:34])([CH3:33])[C:28]([CH3:35])([CH3:27])[O:29]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 58679063methyl 6-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (2.00 g, 5.84 mmol) in 1,4-dioxane (20 ml) was added triethylamine (3.20 ml, 22.9 mmol). 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (2.50 ml, 17.2 mmol) was added dropwise under an argon stream and the mixture was stirred at room temperature for 30 min. To the mixture were added 2-(dicyclohexylphosphino)biphenyl (245 mg, 0.699 mmol) and palladium acetate(II) (39.0 mg, 0.173 mmol) under an argon stream, and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and saturated aqueous ammonium chloride solution was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. A mixed solvent of hexane-ethyl acetate (10:1) was added to the obtained residue and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to give methyl 6-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.66 g, yield 74%).

Workup

  1. stirringthe mixture was stirred at 100° C. for 2 hr
  2. temperatureto cool to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. additionA mixed solvent of hexane-ethyl acetate (10:1) was added to the obtained residue
  9. filtrationthe precipitated solid was collected by filtration
  10. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-b9a56904b014450bbbf17e573af71757
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

Loading…