Hexane → HCID 22032645, compound

HRID 887224Notes

Reaction equation

HRID 887224 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[C:8]([NH2:12])[CH:7]=[CH:6][CH:5]=2.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]=[C:22]=[O:23])=[CH:16][CH:15]=1.CCCCCC>C1COCC1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([NH:12][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[C:10]([CH3:11])=[C:2]([CH3:1])[NH:3]3)=[O:23])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 43746174-Bromobenzyl isocyanateHCID 220325962,3-Dimethyl-1H-indol-4-amine

Product 1

HCID 22032645HCID 22032645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3-Dimethyl-4-aminoindole (0.11 g, 0.7 mmol) in THF (3 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.17 g, 0.8 mmol) at ambient temperature. After stirring for 3 hours at ambient temperature, hexane was added to the reaction mixture to precipitate the title compound as a tan solid (0.12 g). mp 190° C. 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 3H), 2.25 (s, 3H), 4.25 (d, 2H), 6.51 (t, 1H), 6.82 (t, 1H), 6.85 (d, 2H), 6.95 (m, 2H), 7.25 (d, 2H), 7.53 (d, 2H), 7.78 (s, 1H), 11.04 (s, 1H); MS (DCI+) m/z 346 (M+H)+; Anal. Calcd. for C18H18N3BrO: C, 58.08; H, 4.87; N, 11.29. Found: C, 57.97; H, 4.92; N, 11.30.

Workup

  1. customto precipitate the title compound as a tan solid (0.12 g)

Sources & evidence

ORD record
ord-2dbd25129f5b46f28380f06f6b239414
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

Loading…