Potassium Carbonate → 4-((6-(3-Fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

HRID 40177

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Cl[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([CH2:21][O:22][C:23]3[C:32]4[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=4)[N:26]=[CH:25][CH:24]=3)=[N:19][N:20]=2)[N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.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].C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([CH2:21][O:22][C:23]4[C:32]5[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=5)[N:26]=[CH:25][CH:24]=4)=[N:19][N:20]=3)[N:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-fluorophenylboronic acid (0.092 g, 0.66 mmol) was added to a suspension of 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (0.150 g, 0.44 mmol) in 2.5 mL dimethylformamide, followed by the addition of potassium carbonate (0.18 g, 1.3 mmol) in 0.6 mL water. PdCl2(dppf)-CH2Cl2 adduct (0.018 g, 0.022 mmol) was added and the flask was purged with argon, sealed and heated at 80° C. for four hours. Purification by MPLC (eluted with 5 then 10% MeOH in CH2Cl2) afforded the product as an off-white solid (78 mg, 44%). (ESI, pos. ion) m/z: 402.1 (M+H).

Workup

customthe flask was purged with argon
customsealed
customPurification by MPLC (
washeluted with 5

Sources & evidence

ORD record: ord-67a6ae8489094008958c3a4635469c13
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Linked notes

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