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

HRID 1684939

Reaktionsgleichung

Reaktionsgleichung von HRID 1684939
[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

Komponenten

7

Edukt 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×

Produkt 1

HCID 67263269methyl 3-(2-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido)benzoateAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-db58808ff8374dd4a70ad8f0ff973894
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148361B2

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