Sulfuric Acid → 3-(1-Methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid

HRID 1888540ノート

反応式

HRID 1888540 の反応式
C[O:2][C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][C:16](Br)=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=[O:4].[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.S(=O)(=O)(O)O>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][N:20]1[CH:24]=[C:23]([C:16]2[CH:15]=[N:14][C:9]3[NH:10][C:11]4[CH:12]=[N:13][C:5]([C:3]([OH:2])=[O:4])=[CH:6][C:7]=4[C:8]=3[CH:17]=2)[CH:22]=[N:21]1

参加物

7

反応物 3

HCID 1118Sulfuric AcidHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58266719Methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c']dipyridine-6-carboxylate

生成物 1

HCID 683470063-(1-Methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
140 °C

実験手順

A degassed mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (30.4 mg, 99.3 μmmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (31.0 mg, 0.149 mmol), and bis(triphenylphosphine)palladium(II) dichloride (3.5 mg, 5.0 μmol) in acetonitrile (2.5 mL) and 2N aqueous sodium carbonate solution (2.5 mL) was heated under microwave irradiation at 140° C. for 10 minutes. The cooled reaction mixture was acidified with 10% aqueous sulfuric acid, the solid removed by filtration and the resultant filtrate purified by preparative HPLC (0-30% MeCN over 30 min, 35 mL/min) to afford the title compound. 1H NMR (DMSO-D6, 500 MHz): 12.84 (s, 1H), 9.04 (d, J=2.1 Hz, 1H), 8.95 (s, 2H), 8.91 (d, J=2.1 Hz, 1H), 8.25 (s, 1H), 8.00 (s, 1H), 6.48 (s, 1H), 3.92 (s, 3H). LCMS (Method D): RT=5.24 min, M+H+=294.

後処理

  1. customThe cooled reaction mixture
  2. customthe solid removed by filtration
  3. customthe resultant filtrate purified by preparative HPLC (0-30% MeCN over 30 min, 35 mL/min)

出典と根拠

ORDレコード
ord-94978f9ca18c4237bd4fde2ac0f0832c
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

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