Triethylamine → N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-ylmethyl)acrylamide

HRID 1690331Notes

Reaction equation

HRID 1690331 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9](CNC)=[CH:8]1.[CH2:19]([N:21](CC)[CH2:22]C)C>C(Cl)Cl>[CH3:19][N:21]([CH2:22][C:8]1[N:7]([CH3:6])[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1)[C:1](=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22139044methyl({1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl}methyl)amine

Product 1

HCID 66905356N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-ylmethyl)acrylamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acryloyl chloride (0.43 g, 5.58 mmole) in CH2Cl2 (10 mL) was added dropwise with stirring to a solution of 1-methyl-3-(methylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (0.93 g, 5.28 mmole) and triethylamine (0.8 mL, 5.8 mmole) in CH2Cl2 (40 mL) at 0° C. under N2. The reaction was allowed to warm to RT and stir for 1 hr, then was concentrated in vacuo. The residue was dissolved in 10% NaOH and extracted with CH2Cl2 (3×20 mL). The extracts were dried (MgSO4), filtered, and concentrated. The residual oil was flash chromatographed on silica gel (5% MeOH/CH2Cl2) to give the title compound (1.0 g, 80%) as a colorless oil: MS (ES) m/e 216 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in 10% NaOH
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1fab533534c74b93a8e2f2c447027c40
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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