Triethylamine → HCID 86699758, 화합물

HRID 515193노트

반응식

HRID 515193 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 86699758HCID 86699758, 화합물수율 75.2%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-356a8412f95845ffa6fa99d988fb1729
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108936B2

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