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

HRID 2264203Notes

Reaction equation

HRID 2264203 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 99.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 0.2 g, 0.71 mmol) in pyridine (2 mL), 0.071 mL (0.78 mmol) of 3-fluoro-4-methylbenzoyl chloride were added. The mixture was heated at 40° C. for 4 h and the solvent was evaporated. The crude mixture was extracted between ethyl acetate and water, the organic layer was dried (MgSO4) and evaporated to give the title compound (0.295 g, 88% of yield) which was used in the next step without further purification.

Workup

  1. customthe solvent was evaporated
  2. extractionThe crude mixture was extracted between ethyl acetate and water
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1c6b33a970b545aa8d2fd52c6a36b25c
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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