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

HRID 1684939

反応式

HRID 1684939 の反応式
[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

参加物

7

反応物 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 acid2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-db58808ff8374dd4a70ad8f0ff973894
出典データセット
uspto-grants-2012_04
特許番号
US08148361B2

関連ノート

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