3-Fluorobenzylamine → HCID 76285218, compound

HRID 1770665Notes

Reaction equation

HRID 1770665 reaction equation
[CH2:1]([S:3][C:4]1[C:13]([C:14](OCC)=[O:15])=[C:12]([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:20]([F:23])([F:22])[F:21])=[CH:9][N:10]=2)[N:5]=1)[CH3:2].C[Al](C)C.[F:28][C:29]1[CH:30]=[C:31]([CH2:35][NH2:36])[CH:32]=[CH:33][CH:34]=1>C1(C)C=CC=CC=1.O>[CH2:1]([S:3][C:4]1[C:13]([C:14]([NH:36][CH2:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([F:28])[CH:30]=2)=[O:15])=[C:12]([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:20]([F:23])([F:21])[F:22])=[CH:9][N:10]=2)[N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 668533-FluorobenzylamineHCID 16682925TrimethylaluminumHCID 86720178HCID 86720178, compound

Product 1

HCID 76285218HCID 76285218, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 2-(ethylthio)-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.20 g, 0.58 mmol, 1 eq.) in toluene (6 ml) were added Me3Al(2M solution in toluene, 1.16 ml, 2.32 mmol, 4 eq.) and (3-fluorophenyl)methanamine (0.27 ml, 2.32 mmol, 4 eq.) at RT. The reaction mixture was stirred at 110° C. for 16 h. Afterwards the mixture was diluted with water (50 ml) and was extracted with EtOAc (3×40 ml). The combined organic layers were washed with a 0.5 M aq. HCl (60 ml), brine (60 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which was purified by CC (EtOAc/hexane 1:4) to yield 2-Ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-[1,5]naphthyridine-3-carboxylic acid amide (example 1) (0.14 g, 0.33 mmol, 57%). MS m/z [M+H]+ 424.1.

Workup

  1. extractionwas extracted with EtOAc (3×40 ml)
  2. washThe combined organic layers were washed with a 0.5 M aq. HCl (60 ml), brine (60 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated
  5. customto provide the crude product, which
  6. customwas purified by CC (EtOAc/hexane 1:4)

Sources & evidence

ORD record
ord-6453d3c1f17240a894b4ea4a45b041b0
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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