Methanol → HCID 54312816, compound

HRID 1738331Notes

Reaction equation

HRID 1738331 reaction equation
[CH:1]1([N:6]([C@@H:11]2[CH2:16][C:15]3[C:17](OS(C(F)(F)F)(=O)=O)=[CH:18][CH:19]=[C:20]([F:21])[C:14]=3[O:13][CH2:12]2)[CH:7]2[CH2:10][CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:37][OH:38].[C]=O.CN([CH:44]=[O:45])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]1([N:6]([C@@H:11]2[CH2:16][C:15]3=[C:17]([C:37]([O:45][CH3:44])=[O:38])[CH:18]=[CH:19][C:20]([F:21])=[C:14]3[O:13][CH2:12]2)[CH:7]2[CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 54348562HCID 54348562, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 54312816HCID 54312816, compound

Reagents, catalysts & solvents 2

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

(R)-3-(N-Cyclopentyl-N-cyclobutylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran (0.67 g, 1.5 mmol) (4), DMF (20 mL), triethylamine (0.6 g, 6 mmol), methanol (0.8 g, 12.7 mmol), palladium(II)acetate (22 mg, 0.1 mmol) and 1,3-bis(diphenylphosphino)propane (44 mg, 0.1 mmol) were placed in a round-bottomed flask. The solution was stirred at 75° C. in an atmosphere of carbon monoxide for 4 h. The solvent was removed in vacuo, the residue was dissolved in diethyl ether and treated with active charcoal. Evaporation of the solvent afforded 380 mg of the title compound as an uncolored oil. GC/MS (70 eV) M=347 (3 %).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in diethyl ether
  3. additiontreated with active charcoal
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e71bc2133831460e907dbdde066593cf
Source dataset
uspto-grants-1999_10
Patent number
US05962514

Reaction notes

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