Potassium Phosphate, Tribasic → HCID 90333923、化合物

HRID 595708ノート

反応式

HRID 595708 の反応式
Br[C:2]1[C:3](=[O:9])[NH:4][NH:5][C:6](=[O:8])[CH:7]=1.[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14](B(O)O)[NH:15]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:2]1[C:3](=[O:9])[NH:4][NH:5][C:6](=[O:8])[CH:7]=1)[NH:15]2

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 2549424-Bromopyridazine-3,6-diolHCID 90333436HCID 90333436、化合物

生成物 1

HCID 90333923HCID 90333923、化合物収率 40.8%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a degassed solution of 4-bromo-1,2-dihydropyridazine-3,6-dione (100 mg, 0.5 mmol), (4-fluoro-1H-indol-2-yl)boronic acid (131 mg, 0.7 mmol) and K3PO4 (279 mg, 1.1 mmol) in DMF (2 mL) and H2O (0.2 mL) was added Pd(dppf)Cl2 (5 mg) under N2. The mixture was stirred at 80° C. for 12 h. After the solvent was removed, the residue was purified by prep-TLC (DCM:EtOAc=10:1) to give the product of 4-(4-fluoro-1H-indol-2-yl)-1,2-dihydropyridazine-3,6-dione (50 mg, yield: 39%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.95 (br. s, 1H), 7.47˜7.68 (m, 3H), 7.35 (d, J=8.0 Hz, 1H), 7.11˜7.19 (m, 1H), 6.81 (dd, J=8.0, 10.4 Hz, 1H). MS (M+H)+: 246.

後処理

  1. customAfter the solvent was removed
  2. customthe residue was purified by prep-TLC (DCM:EtOAc=10:1)

出典と根拠

ORDレコード
ord-8e7c892558a24affa9fe7259afa67314
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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