3-Chloro-4-methoxyaniline → 2-Oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxyphenyl)amide

HRID 49134

反応式

HRID 49134 の反応式
[O:1]=[C:2]1[CH2:10][C:9]2[C:8]([C:11]([OH:13])=O)=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[Cl:14][C:15]1[CH:16]=[C:17]([NH2:23])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([NH:23][C:11]([C:8]2[C:9]3[CH2:10][C:2](=[O:1])[NH:3][C:4]=3[CH:5]=[CH:6][CH:7]=2)=[O:13])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

参加物

7

反応物 3

HCID 214413-Chloro-4-methoxyanilineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 103973292-oxo-2,3-dihydro-1H-indole-4-carboxylic acid

生成物 1

HCID 701606642-Oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxyphenyl)amide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (200 mg, 1.13 mmol) and 3-chloro-4-methoxy-phenylamine (178 mg, 1.13 mmol) in dimethylformamide (15 mL) at room temperature benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent 997 mg, 2.26 mmol) was added followed by 4-dimethylaminopyridine (206 mg, 1.69 mmol). The mixture was stirred at room temperature for 72 hours. The reaction was then diluted with ethyl acetate (300 mL), washed with saturated sodium bicarbonate solution (100 mL), water, 2N hydrochloric acid (100 mL), water (3×200 mL) and brine, dried (over magnesium sulfate) and concentrated. The residue was triturated with ethyl acetate to give 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxy-phenyl)-amide as a tarnish-pink solid.

後処理

  1. washwashed with saturated sodium bicarbonate solution (100 mL), water, 2N hydrochloric acid (100 mL), water (3×200 mL) and brine
  2. dry with materialdried (over magnesium sulfate)
  3. concentrationconcentrated
  4. customThe residue was triturated with ethyl acetate

出典と根拠

ORDレコード
ord-817f487d9a8347ca899d29c8e426e9bb
出典データセット
uspto-grants-2004_03
特許番号
US06706709B2

関連ノート

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