Dimethylformamide → HCID 68716201, compound

HRID 29419Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15](I)=[C:14]([O:19][CH3:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][N:22](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>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([C:21]#[N:22])=[C:14]([O:19][CH3:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To 5-iodo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester (490 mg, 1.26 mmol) was added 356 mg (3 mmol) of Zn(CN)2, 140 mg of Pd(PPh3)4 and 4 mL of DMF. The mixture was stirred at 90° C. for 3 h. After cooling to room temperature the reaction mixture was loaded onto a silica gel column and was purified by column chromatography to give 260 mg (72% yield) of desired 5-cyano-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was obtained as a white solid.

Workup

temperatureAfter cooling to room temperature the reaction mixture
customwas purified by column chromatography

Sources & evidence

ORD record: ord-707c980154ff4b51afb95eb24d0df3a1
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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