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Methyl iodide → methyl 3-cyclohex-1-en-1-yl-1H-indole-6-carboxylate

HRID 421933
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HRID 421933 반응식
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:19]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

생성물 1

HCID 57362688methyl 3-cyclohex-1-en-1-yl-1H-indole-6-carboxylate수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
20 °C

실험 절차

A solution (0.1 M) of 3-cyclohex-1-en-1-yl-1H-indole-6-carboxylic acid (prepared as described in International patent application publication WO2004/087714) in dry DMF was cooled to 0° C. and treated with K2CO3 (1.05 eq). A solution (3 M) of MeI (1.05 eq) in DMF was then added over 0.5 h, and the temperature was raised to 20° C. After 18 h, the reaction was quenched with aqueous HCl(1N) and diluted with EtOAc. The organic phase was separated and washed several times with aqueous HCl(1N), then with brine. The dried organics were concentrated to give the title compound (99%) as a solid; (ES+) m/z 256 (M+H)+.

후처리

  1. customthe reaction was quenched with aqueous HCl(1N)
  2. additiondiluted with EtOAc
  3. customThe organic phase was separated
  4. washwashed several times with aqueous HCl(1N)
  5. concentrationThe dried organics were concentrated

출처 및 근거

ORD 기록
ord-cf1e7e5c6e9b493996265548a5598888
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101595B2

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