Methanol → HCID 44447719, compound

HRID 1866854Notes

Reaction equation

HRID 1866854 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][C:8]=1[C:25]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][CH:29]2[CH2:31][CH:26]1[CH2:27][CH2:28]2)(=O)=O.[CH2:40](N(CC)CC)C.[C]=O.[OH2:49].[CH3:50][OH:51]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:32]1([C:25]2([C:8]3[CH:9]=[C:10]([O:13][CH2:14][C:15]4[CH:24]=[CH:23][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[N:16]=4)[CH:11]=[CH:12][C:7]=3[C:50]([O:51][CH3:40])=[O:49])[CH2:30][CH:29]3[CH2:31][CH:26]2[CH2:27][CH2:28]3)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

9

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 57978641HCID 57978641, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 44447719HCID 44447719, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2a (280 mg, 0.50 mmol) in DMF (4.8 mL) and methanol (4.8 mL) were added successively palladium (II) acetate (12.0 mg, 0.05 mmol), dppf (54.0 mg, 0.10 mmol) and triethylamine (0.15 mL, 1.10 mmol). The reaction mixture was saturated with carbon monoxide and then heated to 80° C. under a carbon monoxide atmosphere (balloon) for 18 h. After cooling to room temperature, the reaction mixture was poured into water (20 mL) and extracted three times with EtOAc. The combined organic extracts were washed three times with water, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; hexane/EtOAc 9:1) give a solid (122 mg) that was triturated with ether/hexane to provide 2b as a solid (62 mg), m.p. 106-107° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times with EtOAc
  3. washThe combined organic extracts were washed three times with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b3213adc280459db7540a005e5b9b67
Source dataset
uspto-grants-2009_12
Patent number
US07629467B2

Reaction notes

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