Dimethylformamide → HCID 178481057, compound

HRID 2241420Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][N:17]=[C:18](I)[C:11]=12)[NH2:5].[CH3:20][N:21]1[CH2:26]CNC[CH2:22]1.[CH3:27][N:28]([CH:30]=[O:31])[CH3:29]>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]>[NH2:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][N:17]=[C:18]([C:30]([N:28]4[CH2:29][CH2:22][N:21]([CH3:26])[CH2:20][CH2:27]4)=[O:31])[C:11]=23)=[C:2]([F:1])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

3-Fluoro-4-(3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (30 mg, 0.0811 mmol) was dissolved in DMF (1 mL), and 1-methylpiperazine (0.045 ml, 0.405 mmol) and 1,1′-bis(diphenylphosphino) ferrocenedichloropalladium(II) (6.67 mg, 0.0081 mmol) were added. The reaction mixture was purged with N2(g) followed by CO(g) and then held under balloon pressure of CO(g). The mixture was stirred at 70° C. for 18 hours. The crude mixture was partitioned between ethyl acetate and water. The organic layer washed with brine, dried over Na2SO4 and evaporated to afford crude product. The residue was purified by silica gel column chromatography (Biotage 12M) eluting with 5% MeOH/CHCl3 to afford the desired product. Yield: 14 mg at 80% purity, 37%. LRMS (APCI pos) m/e 371.1 (M+H).

Workup

customThe reaction mixture was purged with N2(g)
customThe crude mixture was partitioned between ethyl acetate and water
washThe organic layer washed with brine
dry with materialdried over Na2SO4
customevaporated
customto afford crude product
customThe residue was purified by silica gel column chromatography (Biotage 12M)
washeluting with 5% MeOH/CHCl3

Sources & evidence

ORD record: ord-8f9a0bbb495240449f405a95277a43fb
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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