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

HRID 878372
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HRID 878372 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+].I[CH:40]1[CH2:43][O:42][CH2:41]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][CH:40]1[CH2:43][O:42][CH2:41]1)=[O:31])(=[O:29])=[O:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 133566863-IodooxetaneHCID 136414059N-(4-(2-hydroxyphenyl)-6-methylpyridin-3-yl)-N-methyl-3-(methylsulfonyl)-5-(trifluoromethyl)benzamide

생성물 1

HCID 706634993-Methanesulfonyl-N-methyl-N-{6-methyl-4-[2-(oxetan-3-yloxy)-phenyl]-pyridin-3-yl}-5-trifluoromethyl-benzamide

시약·촉매·용매

2
HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-(4-(2-hydroxyphenyl)-6-methylpyridin-3-yl)-N-methyl-3-(methylsulfonyl)-5-(trifluoromethyl)benzamide (100 mg, 215 μmol) in DMF (2 mL) was added K2CO3 (59.5 mg, 431 μmol) and 3-iodooxetane (43.6 mg, 237 μmol). The reaction mixture was stirred for 2 hours at room temperature followed by stirring 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 (30 mg, 27%). MS (ESI): m/z=521.134 [M+H]+.

후처리

  1. stirringby stirring for 18 hours at 80° C
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  4. washThe organic layers were washed with 30 mL brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe compound was purified by silica gel chromatography on a 10 g column
  9. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

출처 및 근거

ORD 기록
ord-4f6c9a3b26fd48309e4fdc8959fe34ee
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987307B2

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