2-Fluoro-4-nitrophenol → (7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)(4-methylpiperazin-1-yl)methanone

HRID 1400945Notes

Reaction equation

[O-]S([O-])(=O)=O.[Mg+2].Cl[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:18])[S:16][C:9]=12.[F:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[OH:36].C([O-])([O-])=O.[Na+].[Na+]>O(C1C=CC=CC=1)C1C=CC=CC=1.CO.C(Cl)Cl.CCOC(C)=O.CCCCCC.C(Cl)Cl>[F:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[O:36][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:18])[S:16][C:9]=12

Participants

Conditions

Temperature: 190 °C

Procedure

MgSO4 (1.41 g, 11.78 mmol) was added to a suspension of 436 (1.16 g, 3.93 mmol), 2-fluoro-4-nitrophenol (1.23 g, 7.85 mmol) and Na2CO3 (1.24 g, 11.78 mmol) in Ph2O (10 mL). The suspension was heated at 160° C. for 1.5 h and at 190° C. for 2 h. After cooling to room temperature, DCM (30 mL) was added and the reaction mixture was filtered and concentrated. The residue was purified by biotage (SNAP 25 g cartridge; AcOEt/Hexane:10/90 over 5 CV then MeOH/DCM: 0/100 to 10/90 over 20CV), to afford the title compound 437 (1.20 g, 2.88 mmol, 73% yield) as a yellow solid. MS (m/z): 417.2 (M+H).

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered
concentrationconcentrated
customThe residue was purified by biotage (SNAP 25 g cartridge

Sources & evidence

ORD record: ord-de36e8f3bc3641d5a3f0932e1d4670a2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906852B2

Reaction notes

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