Triethylamine → HCID 86699758, compound

HRID 515193Notes

Reaction equation

HRID 515193 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:5]([C:6]([OH:8])=O)=[C:4]([F:13])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.O1CCCC1.CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:5]([C:6]([NH:26][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([Cl:20])=[CH:22][CH:23]=2)=[O:8])=[C:4]([F:13])[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 660364-ChlorobenzylamineHCID 73554900HCID 73554900, compound

Product 1

HCID 86699758HCID 86699758, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 4-bromo-2-fluoro-6-methoxy-benzoic acid (2.5 g, 10.0 mmol) in dichloromethane (30 ml) is added oxalyl chloride (1.04 ml, 12.0 mmol) added drop wise at 0° C. followed by addition of a catalytic amount of dimethylformamide. The mixture is stirred at the same temperature for 2 h. The solution is added via a cannula to a mixture of 4-chloro benzyl amine (1.7 g, 12.0 mmol) and triethyl amine (4.2 ml, 30.0 mmol) in dry tetrahydrofuran (50 ml) at 0° C. After stirring at room temperature for 16 h the mixture is diluted with dichloromethane (50 ml) and washed with water (50 ml), brine (50 ml), dried over sodium sulfate and evaporated in vacuo. The crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane) to obtain 4-bromo-N-[(4-chlorophenyl)-methyl]-2-fluoro-6-methoxy-benzamide (2.8 g, 7.52 mmol, 74%).

Workup

  1. additionadded drop wise at 0° C.
  2. stirringAfter stirring at room temperature for 16 h the mixture
  3. washwashed with water (50 ml), brine (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-356a8412f95845ffa6fa99d988fb1729
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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