Potassium Carbonate → 7-({5-[(1S)-1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-4-phenyl-2H-chromen-2-one

HRID 2116655Notes

Reaction equation

HRID 2116655 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=O)O2)=C[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)([OH:24])[CH2:22][CH3:23].[C:33](=[O:36])([O-])[O-:34].[K+].[K+]>CN1C(=O)CCC1>[OH:24][C@:21]([C:25]1[S:29][C:28]([S:30][C:16]2[CH:15]=[C:14]3[C:13]([C:7]([C:6]4[CH:3]=[CH:2][CH:11]=[CH:10][CH:5]=4)=[CH:8][C:33](=[O:36])[O:34]3)=[CH:18][CH:17]=2)=[N:27][CH:26]=1)([C:20]([F:19])([F:31])[F:32])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866052167-Bromo-3-phenyl-2H-chromen-2-oneHCID 178458806HCID 178458806, compound

Product 1

HCID 111787447-({5-[(1S)-1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-4-phenyl-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

Employing the procedure of Example 1, Step 3, using 7-bromo-phenyl-2H-chromen-2-one (0.331 g, 1.1 mmol), thiol enantiomer #1 (0.243 g, 1 mmol) of Example 7, Step 1, and potassium carbonate (0415 g, 3 mmol) in NMP and heating at 120° C. for 20 h, the title compound was obtained. 1H NMR (400 MHz, acetone-d6): δ 7.88 (s, 1H), 7.45-7.62 (m, 8H), 6.41 (s, 1H), 6.10 (s, 1H, OH), 2.19 (q, 2H), 0.94 (t, 3H).

Sources & evidence

ORD record
ord-c7c8ac44d3a246cf9d13842edd59fdc8
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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