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

HRID 523473Notes

Reaction equation

HRID 523473 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0824a2309d1f493f9cfa72a39b52a34d
Source dataset
uspto-grants-2016_05
Patent number
US09339494B2

Reaction notes

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