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

HRID 921022

反応式

HRID 921022 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-96ffe74c92904414ae1daaeaf32ebb00
出典データセット
uspto-grants-2016_03
特許番号
US09273069B2

関連ノート

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