Water → methyl 3-bromo-1-(3-(methylsulfonyl)propyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 523473ノート

反応式

HRID 523473 の反応式
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].Br[CH2:16][CH2:17][CH2:18][S:19]([CH3:22])(=[O:21])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:16][CH2:17][CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:3]=1[C:11]([O:13][CH3:14])=[O:12]

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 518920821-Bromo-3-methanesulfonylpropaneHCID 67990436methyl 3-bromo-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

生成物 1

HCID 67990438methyl 3-bromo-1-(3-(methylsulfonyl)propyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A suspension of methyl 3-bromo-1H-pyrrolo[3,2-c]pyridine-2-carboxylate 12-c (1000 mg, 3.92 mmol), 1-bromo-3-(methylsulfonyl)propane 12-b (804 mg, 3.92 mmol) and cesium carbonate (1277 mg, 3.92 mmol) in dry DMF (8 ml) was heated at 60° C. for 2 hours. The reaction mixture was then cooled to room temperature and poured into iced water. The product was extracted three times with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by column chromatography using a gradient starting from 0% to 10% MeOH/DCM. After evaporation and drying in vacuo, 750 mg (2.0 mmol, 51.0%) of the target product 12-d was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.10-2.23 (m, 2H) 2.97 (s, 3H) 3.13-3.22 (m, 2H) 3.95 (s, 3H) 4.65 (t, J=7.28 Hz, 2H) 7.75 (dd, J=6.02, 1.00 Hz, 1H) 8.47 (d, J=6.02 Hz, 1H) 8.88 (d, J=1.00 Hz, 1H); m/z=375 (M+H)+, Br pattern.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionThe product was extracted three times with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by column chromatography
  7. customAfter evaporation
  8. customdrying in vacuo
  9. custom750 mg (2.0 mmol, 51.0%) of the target product 12-d was obtained as a white solid

出典と根拠

ORDレコード
ord-0824a2309d1f493f9cfa72a39b52a34d
出典データセット
uspto-grants-2016_05
特許番号
US09339494B2

反応ノート

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