Ethanol → N-cyclopropyl-3-(7-(3-fluoro-2-methoxyphenyl)thieno[2,3-d]pyridazin-2-yl)-4-methylbenzamide

HRID 19583Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:14]([NH:16][CH:17]3[CH2:19][CH2:18]3)=[O:15])[S:8][C:7]=12.[F:24][C:25]1[C:26]([O:34][CH3:35])=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>COCCOC.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH:17]1([NH:16][C:14](=[O:15])[C:13]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:11]([C:9]3[S:8][C:7]4=[C:2]([C:27]5[CH:28]=[CH:29][CH:30]=[C:25]([F:24])[C:26]=5[O:34][CH3:35])[N:3]=[N:4][CH:5]=[C:6]4[CH:10]=3)[CH:12]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-(7-chlorothieno[2,3-d]pyridazin-2-yl)-N-cyclopropyl-4-methylbenzamide (90 mg, 0.26 mmol), 3-fluoro-2-methoxyphenylboronic acid (67 mg, 0.39 mmol), Pd(PPh3)2Cl2 (18 mg, 0.03 mmol), and sodium carbonate (83 mg, 0.78 mmol) in a mixture of DME, ethanol and H2O (7:2:3, 2 ml) was heated to 150° C. for 15 min in the Emrys Optimizer® microwave. The mixture was diluted with MeOH and concentrated over SiO2. Column chromatography (MeOH/CH2Cl2=0→2%) afforded the desired product. Yield: 59 mg. MS (ESI, pos. ion) m/z: 434 (M+1).

Workup

concentrationconcentrated over SiO2

Sources & evidence

ORD record: ord-d9b436b7e4904744ba60e825cd7e082d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745449B2

Reaction notes

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