HCID 69356444, compound → HCID 69359301, compound

HRID 852611Notes

Reaction equation

[CH3:1][CH:2]([C:4]1[C:12]2[C:7](=[C:8]([N+:18]([O-])=O)[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)[NH:6][CH:5]=1)[CH3:3]>CO.O.[Pd]>[NH2:18][C:8]1[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=[C:12]2[C:7]=1[NH:6][CH:5]=[C:4]2[CH:2]([CH3:3])[CH3:1]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of crude ethyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylate (D218) (10.1 g, 28.5 mmol, 1 equiv) in MeOH (250 ml) and H2O (25 ml) was added 10% palladium on charcoal (50% wet, 1.5 g, 8% w/w) and NH4COOH (17 g, 280 mmol, 10 equiv) and the resulting mixture was stirred at 70° C. for 3 h then cooled to room temperature. The catalyst was filtered off through a pad of celite and most of the MeOH was removed in vacuo. The residue was diluted with AcOEt and the organic layer was washed with a saturated NaHCO3 aqueous solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 3/1 to 1/1) gave methyl 7-amino-3-(1-methylethyl)-1H-indole-5-carboxylate (D221) (1.47 g, 21%) as a white solid.

Workup

temperaturethen cooled to room temperature
filtrationThe catalyst was filtered off through a pad of celite and most of the MeOH
customwas removed in vacuo
additionThe residue was diluted with AcOEt
washthe organic layer was washed with a saturated NaHCO3 aqueous solution
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 3/1 to 1/1)

Sources & evidence

ORD record: ord-aad8600c83444802abec574fa3e73606
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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