Triethylamine → 2-(benzyloxy)-N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)benzamide

HRID 1946580ノート

反応式

HRID 1946580 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:24][C:25]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]([C:32]([F:35])([F:34])[F:33])[N:26]=1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:31][C:30]1[C:25]([Cl:24])=[N:26][C:27]([C:32]([F:34])([F:33])[F:35])=[CH:28][CH:29]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18105812-Benzyloxybenzoic acidHCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amine

生成物 1

HCID 597836062-(benzyloxy)-N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)benzamide収率 73%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirring solution of 2-(benzyloxy)benzoic acid (2.55 g, 11.19 mmol) and oxalyl chloride (2.84 g, 22.39 mmol) in THF (20 mL) was added a few drops of DMF (0.012 mL, 0.153 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and further stirred 30 minutes, diluted with toluene and then solvent evaporated. The residue was taken up in THF (20 mL) and to this solution was added 2-chloro-6-(trifluoromethyl)pyridin-3-amine (2.0 g, 10.18 mmol) at 0° C. followed by the addition of triethylamine (4.68 mL, 33.6 mmol). The reaction mixture was allowed to stir 3 days at room temperature then quenched with saturated bicarbonate solution, extracted with EtOAc and solvent evaporated to afford title compound 72 (3.0 g, 73% yield) after purification by flash chromatography (0 to 100% ethyl acetate in hexane). LRMS (ESI): (calc) 406.07 (found) 407.4 (MH)+.

後処理

  1. customsolvent evaporated
  2. customthen quenched with saturated bicarbonate solution
  3. extractionextracted with EtOAc and solvent
  4. customevaporated

出典と根拠

ORDレコード
ord-6445b47fa3ca4492a02727469ffcd765
出典データセット
uspto-grants-2013_03
特許番号
US08399452B2

反応ノート

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