Triethylamine → methyl 3-(2-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido)benzoate

HRID 1684939

반응식

HRID 1684939 반응식
[C:1]1([C:7]2[NH:18][C:10]3=[N:11][CH:12]=[C:13]([C:15]([OH:17])=O)[CH:14]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1.C(N(CC)CC)C.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.O>[C:1]1([C:7]2[NH:18][C:10]3=[N:11][CH:12]=[C:13]([C:15]([NH:28][C:24]4[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=4)[C:21]([O:20][CH3:19])=[O:29])=[O:17])[CH:14]=[C:9]3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 224776352-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid2회

생성물 1

HCID 67263269methyl 3-(2-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido)benzoate수율 26.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (238 mg, 1 mmol, compound B of Example 1) in dimethyl formamide (5 mL) were added sequentially, methyl-3-aminobenzoate (151 mg, 1 mmol), triethylamine (0.1 mL) and BOP (500 mg, 1.2 mmol). After stirring the mixture at RT for 16 h, water was added and the solid formed was filtered, washed sequentially with water, 1N HCl, NaHCO3 and water to afford methyl 3-(2-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido)benzoate (100 mg) as a beige solid. LC/MS; (M+H)+=372.

후처리

  1. customthe solid formed
  2. filtrationwas filtered
  3. washwashed sequentially with water, 1N HCl, NaHCO3 and water

출처 및 근거

ORD 기록
ord-db58808ff8374dd4a70ad8f0ff973894
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148361B2

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