Butylamine → 6-Methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid Butylamide

HRID 1825136Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:14]([OH:16])=O)=[C:8]([CH3:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:27])[CH2:24][CH2:25][CH3:26]>>[CH2:23]([NH:27][C:14]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH3:12])[C:8]=1[CH3:13])=[O:16])[CH2:24][CH2:25][CH3:26]

Participants

Reactant 3

HCID 8007Butylamine

HCID 65578Oxalyl chloride

HCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid2×

Product 1

HCID 207679056-Methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid ButylamideYield 71%

Procedure

This material was prepared from the reaction of 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid (1.12 g, 5.11 mmole) 16c with oxalyl chloride (0.682 ml, 13.6 mmole) and butan-1-amine (1.51 ml, 15.33 mmole) in a manner as previously described for example 16d to give a yellow solid (0.990 g, 71%). 1H NMR (300 MHz, CDCl3) δ 8.01 (1H, d, J=8.6 Hz), 7.31 (1H, dd, J=2.3, 8.6 Hz), 7.25 (1H, d, J=2.3 Hz), 6.32 (1H, s), 4.34 (3H, s), 4.09 (3H, s), 3.95 (2H, m), 3.16 (3H, s), 2.10 (2H, m), 1.92 (2H, m), 1.44 (3H, t, J=7.4 Hz); ESIMS (MH+): 275.15.

Sources & evidence

ORD record: ord-2024e5b8caf64377a66d2e988149d269
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

Loading…