Ammonium Chloride → 5-amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole

HRID 1887707Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1)([O-])=O.[Cl-].[NH4+]>[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 7.4 mL dioxane, 5.5 mL ethanol and 3.7 mL distilled water was added tert-butyl 4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (184 mg, 0.54 mmol). To the mixture was added powdered iron (0) (0.15 g, 5.0 eq) and ammonium chloride (0.885 g, 4.0 eq). The reaction was heated to 70° C. under argon for 3 h. The reaction was cooled and filtered and washed with MeOH. The solvent was removed to obtain the crude which was purified by silica gel chromatography to afford the desired compound tert-butyl 4-(5-amino-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate.

Workup

distillationTo a solution of 7.4 mL dioxane, 5.5 mL ethanol and 3.7 mL distilled water
additionTo the mixture was added
temperatureThe reaction was cooled
filtrationfiltered
washwashed with MeOH
customThe solvent was removed
customto obtain the crude which
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-acd99e5b43f9408ab953a3c42c726947
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501763B2

Reaction notes

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