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

HRID 2426198Notes

Reaction equation

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

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-2aedafd28c91452a8ae53a53a62e4e75
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968540B2

Reaction notes

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