3-Fluoro-4-methylbenzoyl chloride → HCID 59595969, compound

HRID 2264210Notes

Reaction equation

HRID 2264210 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:10][C:11]([NH2:15])=[C:12]([NH2:14])[CH:13]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[CH3:32])[C:26](Cl)=[O:27]>N1C=CC=CC=1>[NH2:15][C:11]1[N:10]=[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:8]([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[F:1])=[CH:13][C:12]=1[NH:14][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:31]([CH3:32])=[C:23]([F:22])[CH:24]=1

Participants

4

Reactant 2

HCID 27348753-Fluoro-4-methylbenzoyl chlorideHCID 595959543''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamine2×

Product 1

HCID 59595969HCID 59595969, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 0.1 g, 0.356 mmol) in pyridine (2 mL), 0.15 g (0.89 mmol) of 3-fluoro-4-methylbenzoyl chloride were added. The mixture was stirred at room temperature overnight and the solvent was evaporated. The crude mixture (0.33 g) was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (0.12 g, 81% of yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude mixture (0.33 g) was purified by silica gel flash chromatography (95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-58575bbe6f644559861722b9bbe8e756
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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