Water → HCID 59177768, compound

HRID 423577Notes

Reaction equation

HRID 423577 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[OH:18].CS(O[CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[O:18][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57930057Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylateHCID 136388465HCID 136388465, compound

Product 1

HCID 59177768HCID 59177768, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-4-[5-(methylsulfonyl)-2-pyridinyl]phenol (0.114 g, 0.43 mmol), 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (0.18 g, 0.55 mmol) and K2CO3 (0.12 g, 0.85 mmol) in DMF (5 mL) was stirred at ambient temperature for 30 min, then heated at 70° C. overnight. Cooled to ambient temperature, the mixture was poured into water (30 mL), and the precipitate was collected, washed with water and air dried. The solid was further triturated with hot MeOH to give 0.125 g (65%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.14 (d, 1H, J=1.7 Hz), 8.23 (dd, 1H, Ja=8.4 Hz, Jb=2.0 Hz), 7.90-7.75 (m, 3H), 7.05 (t, 1H, J=8.4 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.94 (d, 2H, J=6.6 Hz), 3.13 (s, 3H), 2.85-2.70 (m, 2H), 2.15-2.00 (m, 1H), 1.95-1.80 (m, 2H), 1.40-1.25 (m, 2H), 1.24 (d, 6H, J=6.3 Hz); LRMS (ESI), m/z 451 (M+H).

Workup

  1. temperatureheated at 70° C. overnight
  2. temperatureCooled to ambient temperature
  3. customthe precipitate was collected
  4. washwashed with water and air
  5. customdried
  6. customThe solid was further triturated with hot MeOH

Sources & evidence

ORD record
ord-8e531b6867614d0db83592b41b0a7e68
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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