Diethyl Ether → HCID 49853608, 화합물

HRID 2368858노트

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HRID 2368858 반응식
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6](C(OC(C)(C)C)=O)[CH:5]=1)#[N:2].[H-].[Na+].[Cl:24][C:25]1[N:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=1.C(OCC)C>C1COCC1.C(Cl)Cl.CCO>[Cl:24][C:25]1[N:30]=[CH:29][C:28](/[CH:31]=[C:3](/[C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=3)[NH:6][CH:5]=2)\[C:1]#[N:2])=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 27640536-Chloropyridine-3-carbaldehydeHCID 11616206tert-Butyl 3-(cyanomethyl)-5-methoxy-1H-indole-1-carboxylate

생성물 1

HCID 49853608HCID 49853608, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21584144Dichloromethane ethanol용매

실험 절차

To a solution of tert-butyl 3-(cyanomethyl)-5-methoxy-1H-indol-1-carboxylate (4.9 g, 17 mmol, 1.0 eq.) in anhydrous THF (400 mL) was added, under an argon atmosphere, NaH (930 mg, 80%, 31 mmol, 1.8 eq.). The mixture was stirred at room temperature for 10 minutes, and then cooled to 0° C. before the addition of 6-chloro-pyridine-3-carbaldehyde (3 g, 21 mmol, 1.2 eq.). The reaction apparatus was protected from light and the mixture was stirred at room temperature for 1 hour, and then quenched with a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic layer was dried over MgSO4. The solvent was removed under reduced pressure, and the residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 99/1) to afford, after trituration with diethyl ether, the compound (49) as a yellow powder (3.8 g, 72%). TLC: Rf=0.40 (CH2Cl2/EtOH, 96/4); mp: 184° C.; IR νmax (cm−1): 2208 (νCN); 1H NMR (DMSO, 300 MHz) δ (ppm): 3.83 (3H, s, 5′-methoxy), 6.90 (1H, dd, J6′-7′=8.9 Hz, J6′-4′=2.1 Hz, H6′), 7.40 (1H, d, J7′-6′=8.9 Hz, H7′), 7.49 (1H, d, J4′-6′=2.4 Hz, H4′), 7.67 (1H, d, J5″-4″=8.5 Hz, H5″), 7.73 (1H, s, H3), 7.79 (1H, s, H2′), 8.37 (1H, dd, J4″-5″=8.5 Hz, J4″-2″=2.4 Hz, H4″), 8.81 (1H, d, J2″-4″=2.4 Hz, H2″), 11.70 (1H, s, indolic H); 13C NMR (DMSO, 75.5 MHz) δ (ppm): 55.6 (5′-methoxy), 102.0 (C4′), 108.2 (C2), 110.1 (C3′), 112.4 (C6′), 113.2 (C7′), 117.8 (C1), 123.9 (C3a′), 124.2 (C5″), 128.0 (C2′), 130.3 (C3), 130.4 (C3″), 132.3 (C7a′), 137.9 (C4″), 149.8 (C6″), 150.2 (C2″), 154.6 (C5′); ESI-MS: 310.1 ([M+H]+), 334.1 ([M+Na]+); HRESI-MS: m/z 310.0733 (calcd for C17H13N3O35Cl+, 310.0747).

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customquenched with a saturated aqueous ammonium chloride solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 99/1)
  7. customto afford

출처 및 근거

ORD 기록
ord-ec63cabaf85c4f4ea4f1aedda57e47b5
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703808B2

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