Dimethylformamide → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369071Notes

Reaction equation

[CH2:1]([N:3]([CH2:32][CH3:33])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12](I)[CH:13]=2)[C:8]([OH:30])([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:7]1=[O:31])[CH3:2].C([O-])(O)=O.[Na+].[CH3:39][N:40](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:3]([CH2:32][CH3:33])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12]([C:39]#[N:40])[CH:13]=2)[C:8]([OH:30])([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:7]1=[O:31])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole of Example 48 (582 mg, 1, 24 mmol), 60% Zn(CN)2 (172 mg, 0.879 mmol), and (PPh3)4Pd (177 mg, 0.153 mmol) in DMF (6 mL) was stirred for 2.5 h at 80° C. Sat. aqueous NaHCO3 was added. The mixture was extracted with toluene-ethyl acetate, and the extracts were washed with sat. aq. NaHCO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol to give the title compound (382 mg, 66%).

Workup

extractionThe mixture was extracted with toluene-ethyl acetate
washthe extracts were washed with sat. aq. NaHCO3
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol

Sources & evidence

ORD record: ord-aa27f89f86d740ea91140b2d72be943e
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576656B1

Reaction notes

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