Dimethylamine → HCID 22638694, compound

HRID 1836641Notes

Reaction equation

HRID 1836641 reaction equation
CO[N:3]([CH3:21])[C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[C:19]#[N:20])=O.[CH3:22]NC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:22][N:3]([CH2:4][CH:6]1[CH2:8][CH:7]1[CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[C:19]#[N:20])[CH3:21]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86587685HCID 86587685, compound

Product 1

HCID 22638694HCID 22638694, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid methoxy-methyl-amide (0.029 g, 0.13 mmol), dimethylamine (0.7 ml, 1.4 mmol, 2M/THF), and methyl alcohol (5 ml) was treated with sodium triacetoxyborohydride (0.28 g, 1.13 mmol) and stirred at ambient temperature for 1 h. The solution was concentrated in vacuo and the residue applied directly to a silica gel column and eluted with chloroform, methyl alcohol, triethylamine 95:5:0.1 to afford 5-(2-Dimethylaminomethyl-cyclopropylmethyl)-1H-indole-3-carbonitrile (23 mg, 69%) as a light salmon colored solid. 1H-NMR (400 MHz, CDCl3) 8.88 (1H, br s), 7.66 (2H, dd, J=19.4, 2.3 Hz), 7.33 (1H, d, J=8.4 Hz), 7.18 (1H, dd, J=8.4, 1.5 Hz), 2.72 (2H, m), 2.25 (6H, s), 2.24 (2H, m), 0.88 (2H, m), 0.53 (1H, m), 0.45 (1H, m). LC-MS: 0.90; 254.2 (MH)+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washeluted with chloroform, methyl alcohol, triethylamine 95:5:0.1

Sources & evidence

ORD record
ord-c1351e7855f2460d998d5230863a532a
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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