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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
ノート
印刷プレビュー

反応式

HRID 878372 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒

2
HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-4f6c9a3b26fd48309e4fdc8959fe34ee
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987307B2

反応ノート

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