Triethylamine → 6-[3-(Tert-butyl-dimethyl-silanyloxy)-propoxy]-nicotinonitrile

HRID 734435노트

반응식

HRID 734435 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C.[Cl-].[Na+].O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)([CH3:7])([CH3:6])[CH3:5]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 431521396-(3-Hydroxypropoxy)nicotinonitrile

생성물 1

HCID 578454316-[3-(Tert-butyl-dimethyl-silanyloxy)-propoxy]-nicotinonitrile수율 69.5%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of t-butyldimethylsilyl chloride (0.93 g, 6.17 mmol) in CH2Cl2 (25 mL) was added 6-(3-hydroxypropoxy)nicotinonitrile (Example 66, 1 g, 5.61 mmol), Et3N (0.62 g, 6.17 mmol), and DMAP (0.014 g, 0.11 mmol). The mixture was stirred at rt for 18 h. The reaction mixture was diluted with brine and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography (2:1 hexanes/EtOAc) to give the title compound (1.14 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.40 (dd, 1H), 7.69 (dd, 1H), 6.72 (dd, 1H), 4.40 (t, 2H), 3.73 (t, 2H), 1.90-1.98 (m, 2H), 0.82 (s, 9H), 0.02 (s, 6H).

후처리

  1. extractionextracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by silica gel flash chromatography (2:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-c52599b7f28e4e838799b88875c3af98
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592361B2

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