Potassium Phosphate, Tribasic → HCID 90333923, 화합물

HRID 595708노트

반응식

HRID 595708 반응식
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

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2549424-Bromopyridazine-3,6-diolHCID 90333436HCID 90333436, 화합물

생성물 1

HCID 90333923HCID 90333923, 화합물수율 40.8%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8e7c892558a24affa9fe7259afa67314
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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