Pyrrolidine → Ethyl 2-amino-1-benzothiophene-3-carboxylate

HRID 1594229

반응식

HRID 1594229 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=2[S:9][C:10]=1[NH:11]C(=O)C)=[O:5])[CH3:2].N1CCCC1>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 31268PyrrolidineHCID 3722285Ethyl 2-acetamido-1-benzothiophene-3-carboxylate

생성물 1

HCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylate수율 85.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 1b (1.06 g, 4.03 mmol) in toluene (100 mL) was added pyrrolidine (5 mL). The resultant mixture was heated at 100° C. for 8 h, diluted with brine solution (200 mL) and extracted with ethyl ether (300 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4:1) then afforded the title compound (0.76 g, 85%) as a yellow solid: MS (ES) m/z 222 (M+H)+; 1H NMR (400 MHz, CDCl3) δ8.14 (d, J=8.0 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 7.28 (m, 1H), 7.04 (m, 1H), 6.51 (brs, 2H), 4.45 (q, J=7.2 Hz, 2H), 1.50 (t, J=7.2 Hz, 3H).

후처리

  1. extractionextracted with ethyl ether (300 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fe6696ce7fac4bd5885e9d2a8950a16b
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07300952B2

연결된 노트

불러오는 중…