2-Fluoro-4-iodopyridine-3-carbaldehyde → HCID 68058238, compound

HRID 1186821Notes

Reaction equation

HRID 1186821 reaction equation
F[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[C:13]=1[NH:20][NH2:21]>CN(C1C=CN=CC=1)C.CN1C(=O)CCC1>[I:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[N:20]([C:13]3[C:14]([F:19])=[CH:15][C:16]([F:18])=[CH:17][C:12]=3[F:11])[N:21]=[CH:4][C:3]=12

Participants

5

Reactant 2

HCID 99923282-Fluoro-4-iodopyridine-3-carbaldehydeHCID 19778399(2,4,6-Trifluorophenyl)hydrazine

Product 1

HCID 68058238HCID 68058238, compoundYield 16.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
185 °C

Procedure

To a 15 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (530 mg, 2.112 mmol), (2,4,6-trifluorophenyl)hydrazine (359 mg, 2.215 mmol), DMAP (53 mg, 0.434 mmol), and anhydrous NMP (4 mL). The reaction mixture was flushed with argon, securely capped, and heated to 185° C. for 1.75 h. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the product was purified by Biotage Silica gel chromatography using a 40 g Thompson Single Step™ silica cartridge with a linear gradient from 100% hexanes to 100% CH2Cl2 over 14 column volumes to give 133 mg (16.8%) of the title compound as a yellow solid. LC/MS (Condition B): ret. T=3.7 min, (M+H)+ 375.90 and 230 mg (27.6%) of the hydrazone intermediate as a pale yellow solid, LC/MS (Condition B): ret. T=3.7 min, (M+H)+ 395.90.

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-7c053fdf48e0448cacc442e57947929d
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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