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 1690383Notes

Reaction equation

HRID 1690383 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-f93303f11f9a4ec5add9d53e1644a30b
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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