Dimethylformamide → 3-Formyl-1H-indole-7-carbonitrile

HRID 1512724Notes

Reaction equation

CN(C=O)C.[C:6](Cl)(=[O:10])[C:7](Cl)=O.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[C:21]#[N:22])C=[CH:13]1>ClCCl>[CH:6]([C:7]1[C:15]2[C:20](=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][CH:16]=2)[NH:12][CH:13]=1)=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

DMF (0.539 mL) in dry dichloromethane (30 mL) was added dropwise to a solution of oxalyl chloride (0.610 mL) in dry dichloromethane (30 mL) at 0° C. The resulting solution was stirred at 0° C. for 15 min. A solution of 1H-indole-7-carbonitrile (D2) (0.90 g) in dry dichloromethane (5 mL) was added to the reaction mixture. The reaction mixture was warmed to RT and stirred for 30 min. The solvent was evaporated. THF (20 mL) was added, followed by addition of aqueous NaOH (0.5 M, 50 mL). The biphasic mixture was allowed to stand for 10 min. EtOAc (100 mL) and water (70 mL) was added. The organic fraction was separated and was dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 3-formyl-1H-indole-7-carbonitrile (D3) as a light cream solid (0.75 g, 70%). δH (DMSO-d6, 400 MHz): 7.42 (1H, t), 7.79 (1H, dd), 8.43 (1H, dd), 8.48 (1H, s), 10.00 (1H, s), 13.02 (1H, br s). MS (ES): C10H6N2O requires 170; found 171.2 (M+H+).

Workup

temperatureThe reaction mixture was warmed to RT
stirringstirred for 30 min
customThe solvent was evaporated
additionTHF (20 mL) was added
additionfollowed by addition of aqueous NaOH (0.5 M, 50 mL)
waitto stand for 10 min
additionEtOAc (100 mL) and water (70 mL) was added
customThe organic fraction was separated
dry with materialwas dried over anhydrous magnesium sulfate
concentrationThe dried solution was concentrated

Sources & evidence

ORD record: ord-706b4b5cac864b69b567b7c7082fe30f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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