Dimethylformamide → 5-fluoro-3-formyl-1H-indole-6-carbonitrile

HRID 1512848Notes

Reaction equation

[C:1](Cl)(=[O:5])[C:2](Cl)=O.CN(C=O)C.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[C:22]#[N:23])[NH:18][CH:17]=C2.[OH-].[Na+]>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[C:22]#[N:23])[NH:18][CH:17]=[C:2]2[CH:1]=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of oxalyl chloride (0.68 mL) in DCM (10 mL) at 0° C. was dropwise added a solution of DMF (0.60 mL) in DCM (2 mL). The mixture was stirred for 0.5 h at 0° C. and then 5-fluoro-1H-indole-6-carbonitrile (D151) (250 mg) in DCM (3 mL) was added in one portion. The reaction mixture was allowed to warm to rt and stirred overnight. Afterwards, the reaction mixture was added with 2 M aqueous NaOH (30 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and then concentrated under vacuo to give the designed product 5-fluoro-3-formyl-1H-indole-6-carbonitrile (D152) (280 mg), which was used without purification. MS (ES): C10H5FN2O requires 188.0; found 189.1 (M+H+).

Workup

temperatureto warm to rt
stirringstirred overnight
extractionextracted with EtOAc (3×50 mL)
washThe combined organic layers were washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuo

Sources & evidence

ORD record: ord-aa0fb6ee339b42a48bbf7938e6dc4360
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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