Potassium Carbonate → N-[4-(Aminosulfonyl)-2-chlorophenyl]-2-[3-(3-bromo-5-chlorophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]acetamide

HRID 1952364ノート

反応式

HRID 1952364 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:5][C:6]1[C:7](=[O:16])[NH:8][CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].C(=O)([O-])[O-].[K+].[K+].[NH2:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:41])[CH2:39]Br)=[C:33]([Cl:42])[CH:32]=1)(=[O:30])=[O:29]>CN(C)C=O.C(OCC)(=O)C>[NH2:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:41])[CH2:39][N:8]2[CH:9]=[CH:10][C:11]([C:12]([F:15])([F:13])[F:14])=[C:6]([O:5][C:4]3[CH:17]=[C:18]([Cl:20])[CH:19]=[C:2]([Br:1])[CH:3]=3)[C:7]2=[O:16])=[C:33]([Cl:42])[CH:32]=1)(=[O:30])=[O:29]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 584600533-(3-Bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2-olHCID 59511722N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

生成物 1

HCID 42644877N-[4-(Aminosulfonyl)-2-chlorophenyl]-2-[3-(3-bromo-5-chlorophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To 3-(3-bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one (3B, 0.050 g, 0.136 mmol) and potassium carbonate (0.019 g, 0.136 mmol) suspended in dimethylformamide (1 mL) was added N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoacetamide (0.046 g, 0.136 mmol) as a solution in dimethylformamide (1 mL). The reaction mixture was allowed to stir at room temperature. After 16 hours, the reaction mixture was diluted with ethyl acetate (20 mL), washed with water (3×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column, eluting with 0-5% methanol in CH2Cl2 to yield the title compound. 1H NMR (DMSO-d6) δ 10.23 (s, 1H), 8.0 (d, J=8.6 Hz, 1H), 7.96 (d, J=7.2 Hz, 1H), 7.90 (d, J=2.1 Hz, 1H), 7.75 (dd, J=8.6 Hz, J=2.1 Hz, 1H), 7.48-7.44 (m, 2H), 7.44-7.42 (m, 1H), 7.19-7.17 (m, 1H), 7.12-7.10 (m, 1H), 6.66 (d, J=7.2 Hz, 1H), 5.02 (s, 2H). HRMS (M+1)=613.913.

後処理

  1. washwashed with water (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column
  6. washeluting with 0-5% methanol in CH2Cl2

出典と根拠

ORDレコード
ord-3b32b4eade0944f8963fec32eac5aa70
出典データセット
uspto-grants-2013_03
特許番号
US08404856B2

反応ノート

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