Iodoethane → Ethyl 5-(benzyloxy)-6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carboxylate

HRID 2068419노트

반응식

HRID 2068419 반응식
[CH2:1]([O:8][C:9]1[C:14]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:20]=[C:21]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:41](I)[CH3:42]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([N:15]([CH2:41][CH3:42])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:20]=[C:21]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 67217865HCID 67217865, 화합물

생성물 1

HCID 67420223Ethyl 5-(benzyloxy)-6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Ethyl 5-(benzyloxy)-2-(4-fluorophenyl)-6-(methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylate (0.2 g, 0.41 mmol, 1 eq) was dissolved in DMF and cooled to 0° C. Potassium carbonate (0.171 g, 1.6 mmol, 3 eq) was then added and the reaction mixture stirred for 15 minutes. Ethyl iodide (0.037 ml, 0.45 mmol, 1.1 eq) was added slowly dropwise and the resulting mixture was stirred at room temperature for 4 h. The solution was concentrated completely and diluted with water and the product was extracted with dichloromethane twice. The combined organic extracts were washed with water and concentrated yielding the desired product. Yield: 0.16 g (76%). 1HNMR (400 MHz, DMSO-d6): δ 1.07-1.10 (t, J=7.16 Hz, 3H), 1.21-1.24 (t, 3H), 3.04 (s, 3H), 3.64 (m, 2H), 4.19-4.24 (q, J=7.04 Hz, 2H), 5.38 (s, 2H), 7.28 (t, J=8.8 Hz, 2H), 7.42-7.54 (m, 3H), 7.57-7.65 (m, 3H), 7.77-7.95 (m, 2H), 9.02 (s, 1H). LCMS: (ES+) m/z=512.0 (M+H).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 4 h
  2. concentrationThe solution was concentrated completely
  3. additiondiluted with water
  4. extractionthe product was extracted with dichloromethane twice
  5. washThe combined organic extracts were washed with water
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-305e015765094be28e08436b31357059
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293909B2

반응 노트

불러오는 중…