Dimethylformamide → HCID 69896330, compound

HRID 1794285Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]3[C:13]([C:14]4[C:15]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[N:16][O:17][C:18]=4[CH3:19])=[N:12][N:11]=[C:8]32)=[CH:4][CH:3]=1.[CH3:26][N:27](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]=1[C:13]1[N:7]2[CH2:6][C:5]3[C:9]([C:8]2=[N:11][N:12]=1)=[CH:10][C:2]([C:26]#[N:27])=[CH:3][CH:4]=3

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (300 mg) (prepared as in Example 4), zinc cyanide (187 mg), and DMF (5 ml) was degassed with a stream of N2 for 0.5 h. Tetrakis(triphenylphosphine) palladium(0) (20 mg) was added and the reaction heated to 80° C. for 2 days. The reaction mixture was cooled, poured into 10% ammonium hydroxide solution and extracted into EtOAc, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica, eluting with 50% EtOAc/hexane, and recrystallised from EtOAc/hexane to give the title compound (15 mg, 6%). 1H NMR (360 MHz, CDCl3) δ 8.28 (1H, s), 7.69 (1H, dd, J=8.0, 1.4 Hz), 7.54–7.50 (2H, m), 7.48–7.39 (4H, m), 4.05 (2H, s), 2.73 (3H, s), m/z (ES+) 340 (M+H)+.

Workup

customwas degassed with a stream of N2 for 0.5 h
additionTetrakis(triphenylphosphine) palladium(0) (20 mg) was added
temperatureThe reaction mixture was cooled
additionpoured into 10% ammonium hydroxide solution
extractionextracted into EtOAc
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica
washeluting with 50% EtOAc/hexane
customrecrystallised from EtOAc/hexane

Sources & evidence

ORD record: ord-4b37c168c5a74647902c2e2033c4850e
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022724B2

Reaction notes

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