2-Fluoro-4-iodopyridine-3-carbaldehyde → HCID 68058174, compound

HRID 1186817Notes

Reaction equation

HRID 1186817 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](F)[C:3]=1[CH:9]=O.[Cl:11][C:12]1[CH:13]=[C:14]([NH:19][NH2:20])[CH:15]=[C:16]([F:18])[CH:17]=1>CN1C(=O)CCC1>[Cl:11][C:12]1[CH:13]=[C:14]([N:19]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([I:1])=[C:3]3[CH:9]=[N:20]2)[CH:15]=[C:16]([F:18])[CH:17]=1

Participants

4

Reactant 2

HCID 99923282-Fluoro-4-iodopyridine-3-carbaldehydeHCID 53402728(3-Chloro-5-fluorophenyl)hydrazine

Product 1

HCID 68058174HCID 68058174, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 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 (714.6 mg, 2.85 mmol), (3-chloro-5-fluorophenyl)hydrazine (457.6 mg, 2.85 mmol) and anhydrous NMP (8.5 mL). The reaction mixture was flushed with argon, securely capped and heated to 185° C. for 1 h, 45 min. The reaction mixture was worked up according to the procedure described in Intermediate 69A to give 839 mg (76.9%) of the title compound (contains approximately 45% of the hydrazone intermediate) as a dark red solid. LC/MS (Condition B): ret. T=4.8 min, (M+H)+ 373.87.

Workup

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

Sources & evidence

ORD record
ord-809b3987fecf42f0beab85e7fd121cb7
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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