Potassium Carbonate → HCID 86605218, compound

HRID 2116662Notes

Reaction equation

HRID 2116662 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[F:19][C:20]([F:32])([F:31])[C@@:21]([C:25]1[S:29][C:28]([SH:30])=[N:27][CH:26]=1)(O)[CH2:22][CH3:23].C([O-])([O-])=[O:34].[K+].[K+]>CN1C(=O)CCC1>[OH:34][CH2:23][CH2:22][C@H:21]([C:25]1[S:29][C:28]([S:30][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)=[CH:7][C:8](=[O:12])[O:9]3)=[CH:4][CH:3]=2)=[N:27][CH:26]=1)[C:20]([F:32])([F:31])[F:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59814825HCID 59814825, compoundHCID 178458804HCID 178458804, compound

Product 1

HCID 86605218HCID 86605218, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-fluoro-4-pyridin-3-yl-2H-chromen-2-one (0.177 g, 0.73 mmol), (2S)-1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol (0.214 g, 0.88 mmol) and K2CO3 (0.203 g, 1.47 mmol) in NMP was heated at 120° C. overnight. The mixture was cooled to rt and partitioned between aqueous NH4Cl and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue chromatographed on silica gel (toluene/acetone; 95:5 to 80:20) to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.81 (dd, 1H), 8.72 (dd, 1H), 7.82 (dt, 1H), 7.78 (s, 1H), 7.51-7.59 (m, 2H), 7.33-7.40 (m, 2H), 6.42 (s, 1H), 2.74 (br s, 1H), 2.12 (q, 2H), 0.99 (t, 3H).

Workup

  1. temperatureThe mixture was cooled to rt
  2. custompartitioned between aqueous NH4Cl and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was evaporated
  8. customthe residue chromatographed on silica gel (toluene/acetone; 95:5 to 80:20)

Sources & evidence

ORD record
ord-697ee28d275041d8a17f5a91cb2bfe39
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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