2-(Trifluoromethyl)phenylhydrazine → HCID 66668476, compound

HRID 1186819Notes

Reaction equation

HRID 1186819 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](F)[C:3]=1[CH:9]=O.[F:11][C:12]([F:22])([F:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][NH2:20]>CN(C1C=CN=CC=1)C.CN1C(=O)CCC1>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]([F:11])([F:21])[F:22])[N:20]=[CH:9][C:3]=12

Participants

5

Reactant 2

HCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 66668476HCID 66668476, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
185 °C

Procedure

To a dry 15 mL ChemGlass pressure bottle under N2 was added 4-iodo-2-fluoro-3-formylpyridine (750 mg, 2.99 mmol), (2-(trifluoromethyl)phenyl)hydrazine (526 mg, 2.99 mmol), DMAP (200 mg, 1.637 mmol), and anhydrous NMP (4 mL). The reaction mixture was flushed with argon, securely capped and heated at 185° C. for 3.75 h. The reaction mixture was worked up according to the procedure described in Intermediate 69A to give 535 mg (44%) of the title compound (contains approximately 88% of the hydrazone intermediate) as a brown solid. LC/MS (Condition B): ret. T=4.19 min, (M+H)+ 389.90.

Workup

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

Sources & evidence

ORD record
ord-aa3cc72bb0b94da3ac8236828d240a31
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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