5-cyano-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid → 2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 2401174Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:11](C(O)=O)=[C:10]([C:15]([F:18])([F:17])[F:16])[NH:9][C:6]2=[N:7][CH:8]=1)#[N:2]>O.CN1CCCC1=O>[F:18][C:15]([F:16])([F:17])[C:10]1[NH:9][C:6]2=[N:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[C:5]2[CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-Cyano-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (Intermediate 3, 2.49 g, 9.76 mmol) was dissolved in water (36 mL) and N-methyl-2-pyrrolidone (48 mL). The resulting mixture was heated at 120° C. for 18 hours. The reaction mixture was allowed to cool to room temperature and diluted with water. The resulting precipitate was collected by filtration, washed with water and dried under high vacuum at 40° C. for 5 hours to give the title compound as a white solid (1.26 g);

Workup

temperatureto cool to room temperature
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried under high vacuum at 40° C. for 5 hours

Sources & evidence

ORD record: ord-2f28891b36df4361b27dfb5b76c5c03b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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