4-Fluorobenzylamine → HCID 56847777, compound

HRID 242128Notes

Reaction equation

HRID 242128 reaction equation
C(O[C:4]([C:6]1[C:7]([O:18][CH3:19])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[CH:10]=2)=[O:5])C.C[Al](C)C.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1>[F:17][C:11]1[CH:10]=[C:9]2[C:14]([C:15]([CH3:16])=[C:6]([C:4]([NH:30][CH2:29][C:28]3[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=3)=[O:5])[C:7]([O:18][CH3:19])=[N:8]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 673264-FluorobenzylamineHCID 16682925TrimethylaluminumHCID 21226206Ethyl acetate hexaneHCID 66583910HCID 66583910, compound

Product 1

HCID 56847777HCID 56847777, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 400 mg (1.52 mmol) 7-fluoro-2-methoxy-4-methylquinoline-3-carboxylic acid ethyl ester in toluene (10 ml) were added 3.04 ml (2M solution in toluene, 6.1 mmol) Me3Al at RT followed by the addition of 700 μl (6.1 mmol) 4-fluorobenzylamine. The reaction mixture was heated at 110° C. for 16 h. Then the reaction was quenched with water (10 ml) and extracted with EtOAc (3×20 ml). The combined organic layers were washed with water (20 ml), brine (20 ml), dried over Na2SO4 and concentrated in vacuum. After CC (EtOAc/hexane 1:4) of the residue, 160 mg (0.47 mmol, 31%) 7-fluoro-N-[(4-fluorophenyl)-methyl]-2-methoxy-4-methyl-quinoline-3-carboxylic acid amide (example 46) were obtained. MS: m/z 343.1 [M+H]+.

Workup

  1. customThen the reaction was quenched with water (10 ml)
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic layers were washed with water (20 ml), brine (20 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-524ea8cde9df4ca599e3db3bc3ef5c7b
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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