Ethanol → 4-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenylamine

HRID 502274Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)[C:7]([F:17])=[C:6]2[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-].C(O)C>O.[Fe]>[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)[C:7]([F:17])=[C:6]2[C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-cyclopropylmethyl-6-ethoxy-3-fluoro-2-(4-nitro-phenyl)-1H-indole (161 mg, 0.45 mmol), iron powder (170 mg), NH4Cl (170 mg, 3.2 mmol), ethanol (4 mL) and H2O (1.5 mL) were heated at 80° C. for 90 minutes. The reaction mixture was diluted with H2O and was extracted with CH2Cl2. The organic layer was dried and concentrated to provide 4-(1-cyclopropylmethyl-6-ethoxy-3-fluoro-1H-indol-2-yl)-phenylamine (122 mg, 83%) as a white solid.

Workup

extractionwas extracted with CH2Cl2
customThe organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-1f3c5398c01248758b00bfb821390c65
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772271B2

Reaction notes

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