Hydrochloric Acid → HCID 86674581、化合物

HRID 2170626ノート

反応式

HRID 2170626 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2 回HCID 27187797HCID 27187797、化合物HCID 67049717Acetic acid, 2-[4-(bromomethyl)phenoxy]-, methyl ester

生成物 1

HCID 86674581HCID 86674581、化合物収率 61%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-878e9c8360fe40e89bd0f8203ae44a73
出典データセット
uspto-grants-2015_06
特許番号
US09051265B2

反応ノート

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