Potassium Carbonate → 3-Methanesulfonyl-N-methyl-N-{6-methyl-4-[2-(oxetan-3-ylmethoxy)-phenyl]-pyridin-3-yl}-5-trifluoromethyl-benzamide

HRID 878379노트

반응식

HRID 878379 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][C:9]=1[N:15]([CH3:32])[C:16](=[O:31])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:18]=1.C([O-])([O-])=O.[K+].[K+].CC1C=CC(S(O[CH2:50][CH:51]2[CH2:54][O:53][CH2:52]2)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:30][S:27]([C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=1)[C:16]([N:15]([CH3:32])[C:9]1[CH:10]=[N:11][C:12]([CH3:14])=[CH:13][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:50][CH:51]1[CH2:54][O:53][CH2:52]1)=[O:31])(=[O:29])=[O:28]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86670828Oxetan-3-ylmethyl 4-methylbenzene-1-sulfonateHCID 136414059N-(4-(2-hydroxyphenyl)-6-methylpyridin-3-yl)-N-methyl-3-(methylsulfonyl)-5-(trifluoromethyl)benzamide

생성물 1

HCID 706633453-Methanesulfonyl-N-methyl-N-{6-methyl-4-[2-(oxetan-3-ylmethoxy)-phenyl]-pyridin-3-yl}-5-trifluoromethyl-benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution N-(4-(2-hydroxyphenyl)-6-methylpyridin-3-yl)-N-methyl-3-(methylsulfonyl)-5-(trifluoromethyl)benzamide (100 mg, 215 μmol, example 318, intermediate a) in DMF (2 ml) was added K2CO3 (59.5 mg, 431 μmol) and oxetan-3-ylmethyl 4-methylbenzenesulfonate (57.4 mg, 237 μmol). The reaction mixture was stirred for 2 hours at room temperature and for 18 hours at 80° C. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 10 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (87 mg, 76%). MS (ESI): m/z=535.150 [M+H]+.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  3. washThe organic layers were washed with 30 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography on a 10 g column
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

출처 및 근거

ORD 기록
ord-fbbaf037139f486c86e585d0be978996
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987307B2

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