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

HRID 49134

반응식

HRID 49134 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-817f487d9a8347ca899d29c8e426e9bb
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706709B2

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