Water → Ethyl N-(8-bromo-2-methylimidazo[1,2-a]pyridin-7-yl)carbamate

HRID 1951353노트

반응식

HRID 1951353 반응식
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[C:14]([CH3:16])[N:15]=[C:9]2[C:8]=1[Br:17].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:17][C:8]1[C:9]2[N:10]([CH:13]=[C:14]([CH3:16])[N:15]=2)[CH:11]=[CH:12][C:7]=1[NH:6][C:19]([O:21][CH2:22][CH3:23])=[O:20]

참가 물질

7

반응물 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 673603208-Bromo-2-methylimidazo[1,2-a]pyridin-7-amine

생성물 1

HCID 67363252Ethyl N-(8-bromo-2-methylimidazo[1,2-a]pyridin-7-yl)carbamate수율 35%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of sodium bicarbonate (0.74 g, 8.81 mmol) and amine 18 (1.00 g, 4.42 mmol) in 50 mL of dry CH2Cl2 was treated over a period of fifteen minutes with ethyl chloroformate (2.40 g, 22.1 mmol). 4-Dimethylaminopyridine (0.08 g, 0.65 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. Then, water (25 mL) was added and the solution was extracted with CH2Cl2 (3×25 mL). The extracts were dried (Na2SO4), filtered and evaporated under vacuum. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford in order of elution: compound 19 (461 mg, yield: 35%); mp 137-138° C.; 1H NMR (200 MHz, CDCl3) δ 1.34 (t, 3H, J=7 Hz), 2.45 (s, 3H), 4.26 (q, 2H, J=7 Hz), 7.24 (brs, 1H), 7.31 (s, 1H), 7.81 (d, 1H, J=7.4 Hz), 7.92 (d, 1H, J=7.4 Hz); 13C NMR (100 MHz, DMSO-d6) δ 14.1, 14.4, 60.8, 102.5, 109.7, 111.3, 125.1, 133.3, 142.4, 143.0, 153.8. Starting material 18 (0.31 g, 31%).

후처리

  1. extractionthe solution was extracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was purified by chromatography
  6. customv/v) as eluent to afford in order of elution

출처 및 근거

ORD 기록
ord-ada2811d136c490e82ad859af4b64a21
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404707B2

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