Cesium carbonate → HCID 59752593, compound

HRID 749727Notes

Reaction equation

HRID 749727 reaction equation
[CH2:1]([N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][CH2:32][CH2:33][OH:34]>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]2[CH2:15][CH2:14][N:13]([CH2:31][CH2:32][CH2:33][OH:34])[CH2:12][C:11]=2[C:10]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 53325849HCID 53325849, compound

Product 1

HCID 59752593HCID 59752593, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyl-3-(4-chloro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 25; 0.51 g) in DMF (14 mL) was added 1.39 g of Cs2CO3 and 142 μL of 3-bromo-1-propanol. The mixture was stirred at RT for 12 h and then was diluted with water. The aqueous layer was extracted with Et2O and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on SiO2 (2% 2 M NH3 in MeOH/CH2Cl2) afforded 0.15 g of the title compound. The product was dissolved in Et2O and treated with excess 1.0 M HCl in Et2O to afford 0.16 g the corresponding HCl salt. MS (ESI): exact mass calculated for C23H25ClN2O, 380.17; found, m/z 381.2 [M+H]+, 383.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.37-7.27 (m, 7H), 7.19-7.17 (m, 3H), 5.15 (s, 2H), 4.47 (br s, 2H), 3.93-3.25 (m, 6H), 2.94-2.93 (m, 2H), 2.01-1.96 (m, 2H).

Workup

  1. extractionThe aqueous layer was extracted with Et2O
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a2c27fb62774dc685684bb7ff730a95
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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