Dimethylformamide → N-(7-Cyano-2-methyl-benzofuran-4-yl)-2,2-dimethylpropionamide

HRID 501534Notes

Reaction equation

[CH2:1]([C:4]1[C:9]([OH:10])=[C:8]([C:11]#[N:12])[CH:7]=[CH:6][C:5]=1[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:2]=[CH2:3].CN(C=O)C.[Li+].[Cl-]>CC([O-])=O.CC([O-])=O.[Cu+2].Cl[Pd]Cl.O>[C:11]([C:8]1[C:9]2[O:10][C:2]([CH3:3])=[CH:1][C:4]=2[C:5]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:6][CH:7]=1)#[N:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of compound 10D (0.5 g, 1.94 mmol) in a mixed solvent of DMF (2.5 mL) and water (1.9 mL) was added Cu(OAc)2 (1.057 g, 5.82 mmol), followed by a 10 M aqueous solution of LiCl (0.58 mL, 5.8 mmol) and PdCl2 (34.3 mg, 0.194 mmol). The resulting suspension was heated to 100° C. for 1 h. After cooling to rt, the reaction mixture was poured into ice/water, and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The crude product was chromatographed (silica gel) eluting with 10% to 50% EtOAc/hexane to furnish the title compound (0.3 g) as a white foam.

Workup

temperatureAfter cooling to rt
extractionextracted with EtOAc (3×)
washThe combined EtOAc extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude product was chromatographed (silica gel)
washeluting with 10% to 50% EtOAc/hexane

Sources & evidence

ORD record: ord-e865a8803c394d8583b47a6e0d311354
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772267B2

Reaction notes

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