Water → 2-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2061559Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([F:15])([F:14])[F:13])=[C:6]2C(O)=O)#[N:2].O>CN1C(=O)CCC1>[F:15][C:12]([F:13])([F:14])[C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2

Participants

Conditions

Temperature: 135 °C

Procedure

5-cyano-2-(trifluoromethyl)-1H-indole-3-carboxylic acid (Intermediate 13, 2.09 g) was dissolved in NMP (10 mL) and H2O (1 mL) was then added. The mixture was heated to 130-140° C. overnight under nitrogen. The solution was cooled to room temperature and H2O (30 mL) was added and the solution stirred for 40 min. and then filtered. The cake was washed with H2O. The product is then dried under vacuum at 40° C. to give the title compound (1.42 g);

Workup

temperatureThe solution was cooled to room temperature
filtrationfiltered
washThe cake was washed with H2O
customThe product is then dried under vacuum at 40° C.

Sources & evidence

ORD record: ord-a5d6f8507c3b4b8d9e6d0f644a062501
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283365B2

Reaction notes

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