Dimethylamine → dimethyl 1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5,6-dicarboxylate

HRID 1735610Notes

Reaction equation

HRID 1735610 reaction equation
[CH3:1][NH:2][CH3:3].ClC[CH2:6][C:7]1[CH:8]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[C:10]([C:14]([O:16][CH3:17])=[O:15])=[N:11][C:12]=1Cl>CO>[CH3:1][N:2]1[C:12]2=[N:11][C:10]([C:14]([O:16][CH3:17])=[O:15])=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:7]2[CH2:6][CH2:3]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19958230Dimethyl 5-(2-chloroethyl)-6-chloro-2,3-pyridinedicarboxylate

Product 1

HCID 19958232dimethyl 1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5,6-dicarboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethylamine (7.5 g, 166.6 mol) is bubbled into a solution of dimethyl 5-(2-chloroethyl)-6-chloro-2,3-pyridinedicarboxylate (20.0 g, 66mmol) in methanol (400 mL) over three hours. The resulting solution is stirred for 64 hours at room temperature and then four and one-half hours at reflux. After cooling the mixture is concentrated under vacuum and the crude product chromatographed on 250 g silica using 2:1 hexanes:ethyl acetate and then 1:1 hexanes:ethyl acetate as eluant, affording 2.32 g (14%) of dimethyl 1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5,6-dicarboxylate, which is recrystallized from methylene chloride/hexanes, having a melting point 132°-133° C.

Workup

  1. temperaturefour and one-half hours at reflux
  2. temperatureAfter cooling the mixture
  3. concentrationis concentrated under vacuum
  4. customthe crude product chromatographed on 250 g silica using 2:1 hexanes

Sources & evidence

ORD record
ord-a8aa84dcf7a0427ab2a92256f9dc8dd0
Source dataset
uspto-grants-1996_07
Patent number
US05536839

Reaction notes

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