N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine → HCID 178482984, compound

HRID 18312Notes

Reaction equation

HRID 18312 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([O-:14])=O)[CH:8]=2)[NH:3][CH:2]=1.Cl.O=C1CC2C(=CC=C(/C=C/C(O)=O)C=2)N1.[CH3:31][N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([CH2:41][NH:42][CH3:43])=[CH:33]1.CC1NC2C(C=1CNC)=CC=CC=2>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([N:42]([CH3:43])[CH2:41][C:34]3[C:35]4[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:32]([CH3:31])[CH:33]=3)=[O:14])[CH:8]=2)[NH:3][CH:2]=1

Participants

5

Reactant 4

HCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 109867781-Methyl-3-(methylaminomethyl)indoleHCID 66905016(e)-3-(2-Oxo-2,3-dihydro-1h-indol-5-yl)acrylic acid hydrochloride saltHCID 178525338HCID 178525338, compound

Product 1

HCID 178482984HCID 178482984, compoundYield 90%

Procedure

According to the procedure of Example 4, except substituting (E)-3-(3H-imidazo[4,5-b]pyridin-6-yl)acrylate (0.14 g, 0.74 mmole), from Preparation 6, for the (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylic acid hydrochloride salt, and substituting 1-methyl-3-(methylaminomethyl)indole (0.14 g, 0.81 mmole) for the 2-methyl-3-(methylaminomethyl)-1H-indole, the title compound (0.23 g, 89%) was prepared as a light yellow solid: MS (ES) m/e 346 (M+H)+.

Workup

  1. customfrom Preparation 6

Sources & evidence

ORD record
ord-41e2a4d048f7476cae79b41cc40cc93d
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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