2-Hydrazinyl-3-(trifluoromethyl)pyridine → 4-iodo-1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 1186813Notes

Reaction equation

HRID 1186813 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([NH:9][NH2:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[I:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16](F)[C:15]=1[CH:21]=O>CN1C(=O)CCC1>[I:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:9]([C:4]3[C:3]([C:2]([F:1])([F:11])[F:12])=[CH:8][CH:7]=[CH:6][N:5]=3)[N:10]=[CH:21][C:15]=12

Participants

4

Reactant 2

HCID 27777762-Hydrazinyl-3-(trifluoromethyl)pyridineHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 680582364-iodo-1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridineYield 89.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
185 °C

Procedure

To a dry 15 mL ChemGlass pressure bottle under nitrogen was added 3-(trifluoromethyl)pyrid-2-ylhydrazine (499 mg, 2.82 mmol), 4-iodo-2-fluoro-3-formylpyridine (706.8 mg, 2.82 mmol) and anhydrous NMP (4.5 mL). The reaction mixture was flushed with argon, securely capped and heated to 185° C. for 1.5 h. The reaction mixture was worked up according to the procedure described in Intermediate 69A to give 982 mg (89%) of the title compound as an oil. LC/MS (Condition B): ret. T=3.4 min, (M+H)+ 390.94.

Workup

  1. customThe reaction mixture was flushed with argon
  2. customsecurely capped

Sources & evidence

ORD record
ord-6a8cf44a78384077a398e36be658ce12
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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