1-Bromopropane → 5-Chloro-1-propyl-1H-pyrrolo[3,2-b]pyridine

HRID 576589

반응식

HRID 576589 반응식
Br[CH2:2][CH2:3][CH3:4].[Cl:5][C:6]1N=[CH:8][C:9]2[NH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[C:15](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:5][C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][N:14]([CH2:2][CH2:3][CH3:4])[C:9]2=[CH:8][CH:15]=1

참가 물질

5

반응물 3

HCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 457899862-Chloro-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 867126215-Chloro-1-propyl-1H-pyrrolo[3,2-b]pyridine수율 86.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

1-Bromopropane (192 mg, 1.57 mmol) was added to a solution of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg, 1.31 mmol) in DMF (15 mL) followed by cesium carbonate (0.855 g, 2.63 mmol), and the mixture was stirred at 70° C. for 0.5 h. Insoluble solids were filtered off, filtrate was concentrated and partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo to afford title compound (0.22 g, 86%) as an oil. 1H NMR (300 MHz, CDCl3): δ 7.59 (d, J=8.7 Hz, 1H), 7.34 (d, J=3.3 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 6.62 (d, J=3.6 Hz, 1H), 4.07 (t, J=6.9 Hz, 2H), 1.86 (m, 2H), 0.91 (t, J=7.5 Hz, 3H).

후처리

  1. filtrationInsoluble solids were filtered off
  2. concentrationfiltrate was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-b8284f9e9f4242a795d289bd99a40100
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040517B2

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