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Water → 1-Methylethyl 4-[({2-fluoro-4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423577
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HRID 423577 반응식
[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
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57930057Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylateHCID 1363884652-Fluoro-4-[5-(methylsulfonyl)-2-pyridinyl]phenol

생성물 1

HCID 591777681-Methylethyl 4-[({2-fluoro-4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate수율 65%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8e531b6867614d0db83592b41b0a7e68
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101634B2

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