Tetrahydrofuran → HCID 90031761, compound

HRID 56238Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])=[CH:6][CH:5]=1)([O-])=O.C1COCC1.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>[Fe].O>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 64 °C

Procedure

To a mixture of 3-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile (3.0 g, 10.2 mmol), THF (80 mL) and water (40 mL) were added iron powder (2.86 g, 51.2 mmol) and NH4Cl (1.09 g, 20.4 mmol) and the mixture was stirred at 64° C. overnight. The mixture was then cooled to rt and to the resulting mixture was added saturated NaHCO3 aqueous solution. The mixture was filtered and the filtrate was extracted with EtOAc (30 mL×4). The combined organic layers were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (1.76 g, 65%).

Workup

temperatureThe mixture was then cooled to rt and to the resulting mixture
filtrationThe mixture was filtered
extractionthe filtrate was extracted with EtOAc (30 mL×4)
washThe combined organic layers were washed with brine (40 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record: ord-c815e127b0d943b78df202e6c6e475d3
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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