Dimethylformamide → HCID 22171014, compound

HRID 2376244Notes

Reaction equation

Br[CH2:2][CH:3]([C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=1)[CH2:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:6]=1.[C-]#N.[Na+].[CH3:34][N:35](C)C=O>O>[C:20]1([CH3:23])[CH:21]=[CH:22][C:17]([N:7]2[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[CH:9][C:5]([CH2:4][CH:3]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[CH2:2][C:34]#[N:35])=[N:6]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a screw-cap vial were added 3-(3-bromo-2-m-tolyl-propyl)-1,5-di-p-tolyl-1H-pyrazole (prepared by the method of Example 67; 300 mg, 0.65 mmol, 1.0 equiv), sodium cyanide (160 mg, 3.3 mmol, 5.0 equiv) and N,N-dimethylformamide (3.0 mL). The sealed mixture was then heated at 100° C. for 48 h. The reaction mixture was cooled to room temperature, diluted with water (10 mL), and extracted with diethyl ether (3×10 mL). The combined extracts were washed with water (4×10 mL) then brine (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude residue was purified by flash chromatography (25% ethyl acetate/hexanes) giving the desired nitrile (171 mg, 65%). MS (ESI): mass calculated for C28H27N3, 405.22; m/z found, 406.2 [M+H]+.

Workup

customprepared by the method of Example 67
temperatureThe reaction mixture was cooled to room temperature
extractionextracted with diethyl ether (3×10 mL)
washThe combined extracts were washed with water (4×10 mL)
dry with materialbrine (10 mL), dried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude residue was purified by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-9d42683c30a64ad1902aee964706d2fd
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465808B2

Reaction notes

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