Hydrochloric Acid → 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic Acid Methyl Ester

HRID 1814097

반응식

HRID 1814097 반응식
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[O:4].[H-].[Na+].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.Cl>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[O:4]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 735868Methyl 5-(methylsulfonyl)-1H-indole-2-carboxylate

생성물 1

HCID 684447041-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic Acid Methyl Ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of the compound obtained in Example 22 (2) (1.2 g) and N,N-dimethylformamide (23 ml), 60% sodium hydride (204 mg) was added at 0° C. and the mixture was stirred at the same temperature for 20 minutes. To the reaction mixture was added 4-fluorobenzyl bromide (0.65 ml) at 0° C. and the mixture was stirred at 15 to 30° C. for 2 hours. 2N hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (dichloromethane) to obtain 1 g of the desired product in a white amorphous form.

후처리

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred at 15 to 30° C. for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e41012ed824d4c6c81ed997a43671710
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875770B2

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