Potassium Iodide → HCID 11503692, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH:13]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[C:31]([CH3:32])=[C:30](Cl)[N:29]=[CH:28][N:27]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])[CH3:14].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:13]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[C:31]([CH3:32])=[C:30]([O:12][C:3]3[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=3[F:1])[N:29]=[CH:28][N:27]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
2-Fluoro-4-methanesulfonyl-phenol (4) (1.33 g, 7.01 mmol) and 4-(6-chloro-5-methyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester (3) (2.00 g, 6.39 mmol) were dissolved in DMSO (10 mL). To the resulting solution, potassium iodide (0.21 g, 1.27 mmol) and potassium carbonate (0.97 g, 7.01 mmol) were added. The resulting mixture was heated to 130° C. and stirred overnight. The crude was cooled to room temperature, poured into ice water (150 mL) and stirred for 2 h. The precipitate was filtered, washed twice with water (2×10 mL) and dried at 60° C. in a vacuum oven (2.74 g, 91%). The desired product was recrystallized from isopropanol (10 mL) to afford 2.39 g of the title compound (80%).
Workup
- temperatureThe crude was cooled to room temperature
- stirringstirred for 2 h
- filtrationThe precipitate was filtered
- washwashed twice with water (2×10 mL)
- customdried at 60° C. in a vacuum oven (2.74 g, 91%)
- customThe desired product was recrystallized from isopropanol (10 mL)
Sources & evidence
- ORD record
- ord-701167bada044f7980e29243558abc79
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812159B2
Reaction notes
Loading…