2,4-Difluoroaniline → 5-(2,6-difluorophenyl)-2-[(2,4-difluorophenyl)amino]-6H-pyrido[1,2-b]pyridazin-6-one

HRID 1454968Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1.[O-]CCCC.[Na+].[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH2:30]>C1(C)C=CC=CC=1.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.[Fe+2]>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:11]1[C:10](=[O:20])[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:28]=1[F:27])=[N:7]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (100 mg, 0.34 mmol) dissolved in toluene (1.5 mL) was added Pd(DBA) (3.1 mg, 0.0034 mmol), dppf (3.7 mg, 0.0068 mmol), sodium butoxide (23 mg, 0.238 mmol), and 2,4 difluoro aniline (43 mg, 0.34 mmol). The reaction was heated to 80° C. for 3 hours until complete by LCMS analysis. The reaction was passed through celite, condensed to an oil and purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

Workup

customThe reaction was passed through celite, condensed to an oil
custompurified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

Sources & evidence

ORD record: ord-60569d70aaab452487a1c490c2ea6585
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482345B2

Reaction notes

Loading…