N,N-Dimethylethylenediamine → HCID 11417176, compound

HRID 751375Notes

Reaction equation

HRID 751375 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[NH:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 860359201-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde

Product 1

HCID 11417176HCID 11417176, compoundYield 26%

Procedure

1-(4-tert-Butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde is reacted with N,N-dimethylethylenediamine as described in Step 2 of Example 29 to afford 1-(4-tert-butylphenyl)-2-(2-dimethylaminoethylamino)-1H-indole-3-carboxaldehyde (26% yield) as a light tan solid. ESI/MS 364 (M+H); RT 3.39 min. NMR 9.94 (1H, s); 7.84 (1H, br s); 7.67 (2H, d); 7.48 (2H, d, J=9 Hz); 7.10 (1H, t); 6.98 (1H, t); 6.66 (1H, d, J=9 Hz); 3.05 (2H, br s); 2.30 (2H, BR t); 2.03 (6H, S); 1.36 (9H, s).

Sources & evidence

ORD record
ord-d773bdaadf84468d8176daebd210c4c9
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

Loading…