1,2-Dichloroethane → (E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamide

HRID 18311Notes

Reaction equation

HRID 18311 reaction equation
Cl.[O:2]=[C:3]1[CH2:11][C:10]2[C:5](=C[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)[CH:9]=2)[NH:4]1.O.OC1C2N=N[NH:24]C=2C=CC=1.C(N(C(C)C)CC)(C)C.[CH3:37][C:38]1[NH:39][C:40]2[C:45]([C:46]=1[CH2:47][NH:48][CH3:49])=[CH:44][CH:43]=[CH:42][CH:41]=2.C(Cl)CCl>CN(C=O)C>[CH3:49][N:48]([CH2:47][C:46]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][C:38]=1[CH3:37])[C:14](=[O:16])/[CH:13]=[CH:12]/[C:8]1[CH:9]=[C:10]2[CH2:11][C:3](=[O:2])[NH:4][C:5]2=[N:24][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66905016(e)-3-(2-Oxo-2,3-dihydro-1h-indol-5-yl)acrylic acid hydrochloride saltHCID 178526939HCID 178526939, compound

Product 1

HCID 10021425(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylic acid hydrochloride salt (0.50 g, 2.1 mmole), hydroxybenzotriazole monohydrate (0.31 g, 2.3 mmole), diisopropylethylamine (0.80 mL, 4.6 mmole), and 2-methyl-3-(methylaminomethyl)indole (0.40 g, 2.3 mmole) in DMF (50 mL) at RT was added EDC (0.46, 2.3 mmole). After 12 hr the reaction solution was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) to give the title compound (0.66 g, 88%) as a light yellow solid: MS (ES) m/e 361 (M+H)+.

Workup

  1. concentrationAfter 12 hr the reaction solution was concentrated under vacuum
  2. customthe residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH)

Sources & evidence

ORD record
ord-a5bcb270cc6d420182681a528e5abea9
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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