Potassium Phosphate, Tribasic → HCID 54670145, compound
Reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:18][CH2:17][C@H:16]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=4[F:30])[C:15]3=[O:31])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:82][S-:83].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:30][C:21]1[CH:22]=[C:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:24]=[CH:25][C:20]=1[NH:19][C@H:16]1[CH2:17][CH2:18][N:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:4]=[CH:3][C:2]([S:83][CH3:82])=[CH:7][N:6]=3)[CH2:9][CH2:10]2)[C:15]1=[O:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
(S)-1-(1-(5-Bromopyrimidin-2-yl)piperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (Example 7; 0.10 g, 0.20 mmol), Xantphos (0.056 g, 0.098 mmol), K3PO4 (0.11 g, 0.51 mmol), and Pd2 dba3 (0.045 g, 0.049 mmol) were diluted in degassed toluene (3 mL). Sodium methanethiolate (0.032 g, 0.45 mmol) was added and the reaction was stirred at 100° C. overnight. The material was cooled to ambient temperature and flash chromatographed to give (S)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-1-(1-(5-(methylthio)pyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one (0.011 g, 0.023 mmol, 12% yield) as a white solid. Mass spectrum (apci) m/z=480.1 (M+H).
Workup
- temperatureThe material was cooled to ambient temperature
- customflash chromatographed
Sources & evidence
- ORD record
- ord-968057fd309f4d72b9eb7ba3b58bfa0f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754226B2
Reaction notes
Loading…