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

HRID 1951353ノート

反応式

HRID 1951353 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ada2811d136c490e82ad859af4b64a21
出典データセット
uspto-grants-2013_03
特許番号
US08404707B2

反応ノート

読み込み中…