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 1362122Notes

Reaction equation

HRID 1362122 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-9f24e253351f4f8faa309e172b3c89d3
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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