Ammonia → 2-Phenoxymethyl-benzofuran-5-carbonitrile

HRID 1171220Notes

Reaction equation

I[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][C:6]=2[CH:18]=1.N.[CH3:20][N:21]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N>[O:11]([CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:20]#[N:21])=[CH:18][C:6]=2[CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a 1-methyl-2-pyrrolidinone (10 mL) solution of 5-iodo-2-phenoxymethyl-benzofuran (250 mg, 0.714 mmol) described in Production Example 75-1-1 were added zinc cyanide (168 mg, 1.43 mmol) and tetraquis(triphenylphosphine) palladium (0) (165 mg, 0.143 mmol). This mixture was stirred at 130° C. for 3 hours. After adding ice water and concentrated aqueous ammonia to the reaction mixture and stirring, the reaction mixture was extracted with ethyl acetate. The organic layer was separated followed by washing with sat. NaCl, drying over anhydrous magnesium sulfate and concentrating under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (27 mg, 15%).

Workup

stirringstirring
extractionthe reaction mixture was extracted with ethyl acetate
customThe organic layer was separated
washby washing with sat. NaCl
dry with materialdrying over anhydrous magnesium sulfate
concentrationconcentrating under a reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-df0de7e5065f467997f86bc142b71191
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829585B2

Reaction notes

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