Triethylamine → HCID 22853676, compound

HRID 52265Notes

Reaction equation

HRID 52265 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([N:12]([CH:16]([CH3:18])[CH3:17])[CH2:13][CH2:14][CH3:15])[CH2:7][C:6]=2[C:5](OS(C(F)(F)F)(=O)=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.CN([CH:37]=[O:38])C.[CH3:39][OH:40]>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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]([O:38][CH3:37])=[O:40])=[C:6]2[C:11]=1[O:10][CH2:9][C@H:8]([N:12]([CH:16]([CH3:18])[CH3:17])[CH2:13][CH2:14][CH3:15])[CH2:7]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21901440N,N-dimethylformamide methanolHCID 22853673HCID 22853673, compound

Product 1

HCID 22853676HCID 22853676, compoundYield 71%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

(R)-8-Fluoro-3-(N-isopropyl-N-n-propylamino)-5-trifluoromethanesulfonyloxy-3,4-dihydro-2H-1-benzopyran (2.4 g, 6.0 mmol), triethylamine (1.3 g, 12.9 mmol), 1,3-bis (diphenylphosphino)propane (95 mg, catalytic amount), palladium(II)acetate (48 mg, catalytic amount) and DMF/MeOH (30 mL, 3:1) were mixed in a 50 mL three necked round bottom flask. The flask was evacuated followed by the inlet of CO (repeated two times). The reaction mixture was stirred at 70° C. for 7.5 hours. The solvent was removed in vacuo and the residue was dissolved in diethyl ether/sat. NaHCO3. The layers were separated and the water phase was extracted once with ether. The combined ether layers were dried (MgSO4) and the solvent was removed in vacuo to give a crude which was purified by flash chromatography (SiO2, hexane/EtOAC, 9:1) to give 1.3 g of the title compound (71% yield).

Workup

  1. customThe flask was evacuated
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in diethyl ether/
  4. customThe layers were separated
  5. extractionthe water phase was extracted once with ether
  6. dry with materialThe combined ether layers were dried (MgSO4)
  7. customthe solvent was removed in vacuo
  8. customto give a crude which
  9. customwas purified by flash chromatography (SiO2, hexane/EtOAC, 9:1)

Sources & evidence

ORD record
ord-ebaa620267364b91bb19db5576e12268
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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