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

HRID 1506001노트

반응식

HRID 1506001 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매HCID 10340Sodium Carbonate용매

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온도
140 °C

실험 절차

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 μmol), 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-18262a7123fe4d65acd88e7779efdc11
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216980B2

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