Potassium Phosphate, Tribasic → 6-(4-Methoxy-phenyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796640Notes

Reaction equation

O[C:2]1[C:3]([CH3:27])=[C:4]2[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[C:8]([C:24]#[N:25])[CH:7]=[N:6][N:5]2[CH:26]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[C:3]([CH3:27])=[C:4]3[C:9]([NH:10][C:11]4[CH:12]=[CH:13][C:14]([O:17][C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)=[CH:15][CH:16]=4)=[C:8]([C:24]#[N:25])[CH:7]=[N:6][N:5]3[CH:26]=2)=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of Example 397 (24 mg, 0.049 mmol), 4-methoxybenzeneboronic acid (11 mg, 0.072 mmol), Pd(OAc)2 (1.0 mg, 0.0045 mmol), 2-(dicyclohexylphosphino) biphenyl (5.0 mg, 0.014 mmol) and K3PO4 (20 mg, 0.10 mmol) in toluene (0.5 ml) was degassed with argon. The mixture was heated at 90° C. for 20 min, then directly purified by silica gel flash column chromatography to give title compound (20 mg, 92%) (10% EtOAc—hexanes). LCMS Found: (M+H)+=447.2

Workup

customdirectly purified by silica gel flash column chromatography

Sources & evidence

ORD record: ord-ed0ca486ec5c41e89923b8dc52749493
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030112B2

Reaction notes

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