HCID 2777968, compound → HCID 66668290, compound

HRID 1186810Notes

Reaction equation

HRID 1186810 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][NH2:11].[I:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15](F)[C:14]=1[CH:20]=O>CN1C(=O)CCC1>[I:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[N:10]([C:3]3[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=3[F:1])[N:11]=[CH:20][C:14]=12

Participants

4

Reactant 2

HCID 2777968HCID 2777968, compoundHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 66668290HCID 66668290, compoundYield 20.4%

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 (2,3,4-trifluorophenyl)hydrazine (359 mg, 2.212 mmol), 4-iodo-2-fluoro-3-formylpyridine (555.1 mg, 2.212 mmol), and anhydrous NMP (5 mL). The reaction mixture was flushed with argon, securely capped, and heated at 185° C. for 3 h. The reaction mixture was worked up according to the procedure described in Intermediate 69A. The product was purified by Biotage Silica gel chromatography using a 25 g Thompson Single Step™ silica cartridge with a linear gradient from 100% hexanes to 100% CH2Cl2 over 12 column volumes gave 162.9 mg (20.4%) of the title compound as a yellow solid. LC/MS (Condition B): ret. T=4.0 min, (M+H)+ 375.93.

Workup

  1. customThe reaction mixture was flushed with argon
  2. customsecurely capped
  3. customThe product was purified by Biotage Silica gel chromatography

Sources & evidence

ORD record
ord-1f5a3857243a4b25946c85cf391944a9
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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