Water → 2-Tert-butyl-6-fluoro-5-nitro-1H-indole

HRID 1964268Notes

Reaction equation

[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([F:14])=[CH:7][C:6]=1[NH:15]C(=O)CCC.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>CN(C=O)C>[C:2]([C:3]1[NH:15][C:6]2[C:5]([CH:4]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([F:14])[CH:7]=2)([CH3:22])([CH3:21])[CH3:1]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide (3.0 g, 9.8 mmol) and TBAF (4.5 g, 17.2 mmol) in DMF (25 mL). was heated at 100° C. overnight. The mixture was poured into water and then extracted with EtOAc (80 mL×3). The combined extracts were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give compound 2-tert-butyl-6-fluoro-5-nitro-1H-indole (1.5 g, 65%). 1H-NMR (400 MHz, CDCl3) δ 8.30 (d, J=7.2 Hz, 1H), 7.12 (d, J=11.6 Hz, 1H), 6.35 (d, J=1.2 Hz, 1H), 1.40 (s, 9H).

Workup

extractionextracted with EtOAc (80 mL×3)
washThe combined extracts were washed with water (50 mL) and brine (50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure to dryness
customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1)

Sources & evidence

ORD record: ord-2b3ec2d758094deb9ad4bf540cf0e31c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415387B2

Reaction notes

Loading…