Nitric Acid → tert-Butyl [3-nitro-1-(phenylsulfonyl)-1H-indol-4-yl]acetate

HRID 1094111Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[C:5]1([S:11]([N:14]2[C:22]3[C:17](=[C:18]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OC(=O)C)(=O)C>[N+:1]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[N:14]([S:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)(=[O:12])=[O:13])[CH:15]=1)([O-:4])=[O:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To acetic anhydride (5 mL) at 0° C. was added 90% nitric acid (0.183 mL, 3.90 mmol) and the resulting mixture was aged for 10 min, then added dropwise to a solution of tert-butyl [1-(phenylsulfonyl)-1H-indol-4-yl]acetate from Step B (1.00 g, 2.69 mmol) in acetic anhydride (5 mL) at −78° C. The reaction mixture was stirred at −78° C. for 6 h, then aged at −20° C. for 16 h, then quenched with H2O and extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 70:30, to give the title compound. MS: m/z=361 (M−C4H7).

Workup

waitaged at −20° C. for 16 h
customquenched with H2O
extractionextracted with EtOAc (2×10 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by silica gel chromatography
washeluting with a gradient of hexane

Sources & evidence

ORD record: ord-96366c20630c42be971b7d552efb5a2c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133891B2

Reaction notes

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