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Imidazole → ethyl 7-bromo-3-(3-iodopropyl)-1H-indole-2-carboxylate

HRID 2095252
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HRID 2095252 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18]O.[I:20]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][I:20]
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참가 물질

7

반응물 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 68943187ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate

생성물 1

HCID 68936016ethyl 7-bromo-3-(3-iodopropyl)-1H-indole-2-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a mixture of EXAMPLE 1B (1.116 g) in dichloromethane (30 mL) at 0° C. was added iodine (1.01 g), triphenyl phosphine (1.03 g) and imidazole (0.535 g). The mixture was stirred at 0° C. for 1 hour and treated with saturated NaHCO3 (50 mL). Stirring was continued for 30 minutes, and the organic layer was washed with a saturated aqueous Na2S2O3 (50 mL), water (20 mL), and brine (50 mL) and dried (Na2SO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel (with 0-20% ethyl acetate in hexanes.

후처리

  1. stirringStirring
  2. waitwas continued for 30 minutes
  3. washthe organic layer was washed with a saturated aqueous Na2S2O3 (50 mL), water (20 mL), and brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography on silica gel (with 0-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-c7189dfa8087460a9f97986027d163b8
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445679B2

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