Ammonia → HCID 68615250, compound

HRID 2189132Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([O:17][CH2:18][C:4]=2[CH:3]=1)[CH2:13][CH2:12][CH2:11][N:10]1[CH:14]=[N:15][CH:16]=[C:9]31.[Cu][C:20]#[N:21].N.C(OCC)(=O)C>CN1CCCC1=O>[CH:16]1[N:15]=[CH:14][N:10]2[CH2:11][CH2:12][CH2:13][C:8]3([C:5]4[CH:6]=[CH:7][C:2]([C:20]#[N:21])=[CH:3][C:4]=4[CH2:18][O:17]3)[C:9]=12

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1.93 mmol of 5-bromo-6′,7′-dihydro-3H,5′H-spiro[2-benzofuran-1,8′-imidazo[1,5-a]pyridine] and 9.63 mmol of copper(I) cyanide in 10 ml of N-methyl-pyrrolidone is heated to 150° C. for 72 h. The reaction mixture is cooled to room temperature and poured into a mixture of 25% aqueous ammonia and ethyl acetate. The mixture is stirred vigorously for 15 minutes and the layers are separated. The aqueous layer is extracted with ethyl acetate and the combined organics are washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) followed by crystallization from diethyl ether to afford the title compound as a beige solid. Rf=0.15 (dichloromethane-2M ammonia in ethanol 97:3); Rt=4.66 (gradient II).

Workup

temperatureThe reaction mixture is cooled to room temperature
customthe layers are separated
extractionThe aqueous layer is extracted with ethyl acetate
washthe combined organics are washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue is purified by flash chromatography (SiO2 60 F)
customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record: ord-35d1d8ab65c549719f763cec06982277
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324235B2

Reaction notes

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