Hydrochloric Acid → HCID 86674581, 화합물

HRID 2170626노트

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HRID 2170626 반응식
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[CH:6][CH:5]=2.Br[CH2:19][C:20]1[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1.[H-].[Na+].Cl>CN(C=O)C.C(OCC)(=O)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][O:24][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:3]2[C:4]3[C:9](=[CH:8][C:7]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[CH:6][CH:5]=3)[C:10]([CH3:11])=[C:2]2[CH3:1])=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2회HCID 27187797HCID 27187797, 화합물HCID 67049717Acetic acid, 2-[4-(bromomethyl)phenoxy]-, methyl ester

생성물 1

HCID 86674581HCID 86674581, 화합물수율 61%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the allyl 2,3-dimethyl-1H-indole-5-carboxylate (500 mg, 2.2 mmol) in anhydrous DMF (20 mL) was added the methyl 2-(4-(bromomethyl)phenoxy)acetate (565 mg, 2.2 mmol) followed by NaH (131 mg, 3.3 mmol). The resulting solution was allowed to stir overnight under argon atmosphere. The remaining NaH was hydrolyzed by the careful addition of a 0.5 N HCl solution. The mixture was diluted with ethyl acetate, washed with a 0.5 N HCl solution and brine, dried on MgSO4, and concentrated. The crude residue was purified by chromatography on silica gel (Hexane/Ethyl acetate 5/5) to afford yellow oil (536 mg, 61%). ESI-MS (m/z): 408 [M+H]+

후처리

  1. washwashed with a 0.5 N HCl solution and brine
  2. customdried on MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was purified by chromatography on silica gel (Hexane/Ethyl acetate 5/5)

출처 및 근거

ORD 기록
ord-878e9c8360fe40e89bd0f8203ae44a73
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051265B2

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