Dibutyltin oxide → HCID 178497743, 화합물

HRID 1927419노트

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HRID 1927419 반응식
[C:1]([C:3]1[CH:48]=[CH:47][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].C[Si]([N:53]=[N+:54]=[N-:55])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[NH:53]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:44])([F:45])[F:46])=[CH:39][CH:38]=4)=[CH:33][CH:32]=3)[CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=3)=[CH:47][CH:48]=2)=[N:2][N:55]=[N:54]1

참가 물질

5

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HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831398Methyl E-4-{3-(4-cyanobenzyl)-5-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]pent-4-enyl}benzoate

생성물 1

HCID 178497743HCID 178497743, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

A solution of 295 mg (0.53 mmol) of methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-{[4′-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)pent-4-en-1-yl]benzoate in 20 ml of toluene is mixed with 1.33 ml (9.99 mmol) of trimethylsilyl azide and 249 mg (1 mmol) of di-n-butyltin oxide and heated at 80° C. for 12 hours. After cooling to room temperature, the mixture is washed with saturated sodium bicarbonate solution. The organic phase is separated off, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: dichloromethane→dichloromethane/methanol 10:1). 387 mg (0.56 mmol, 64% of theory) of a white foam are obtained.

후처리

  1. temperatureAfter cooling to room temperature
  2. washthe mixture is washed with saturated sodium bicarbonate solution
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated to dryness
  8. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: dichloromethane→dichloromethane/methanol 10:1)
  9. custom387 mg (0.56 mmol, 64% of theory) of a white foam are obtained

출처 및 근거

ORD 기록
ord-ab3d5267cdb841e381165120d089731a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183271B2

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