Ammonium Chloride → (E)-3-(4-{1-[2-(6-amino-2-tert-butyl-1H-indol-3-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

HRID 1802758Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-])=O)=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:8][CH:7]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][O:2][C:3](=[O:35])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][C:24]([NH2:28])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of (E)-3-(4-{1-[2-(2-tert-butyl-6-nitro-1H-indol-3-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (0.70 g, 1.5 mmol) in ethanol (14 mL) and water (7 mL) was added iron powder (0.74 g, 13 mmol) and ammonium chloride (87 mg, 1.6 mmol) and the resulting mixture was stirred at 85° C. for 1 h. Additional iron powder (820 mg, 14.7 mmol), ethanol (6 mL) and water (3 mL) were added and the reaction was stirred at 85° C. for 50 h. The reaction mixture was filtered and concentrated in vacuo, and the residue was taken up in water. A brown solid precipitate was recovered via vacuum filtration to yield the title compound (0.40 g, 49% yield). LCMS (m/z): 446.0 (M+1).

Workup

stirringthe reaction was stirred at 85° C. for 50 h
filtrationThe reaction mixture was filtered
concentrationconcentrated in vacuo
filtrationA brown solid precipitate was recovered via vacuum filtration

Sources & evidence

ORD record: ord-dd95a666798846fb8fcb877785273ee4
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349883B2

Reaction notes

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