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

HRID 1991685Notes

Reaction equation

HRID 1991685 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)=[CH:7][C:6]=1[NH:15]C(=O)CCC.[CH3:23][C:24]([O-:27])([CH3:26])[CH3:25].[K+].O>CN(C=O)C>[C:24]([O:27][C:8]1[CH:7]=[C:6]2[C:5]([CH:4]=[C:3]([C:2]([CH3:1])([CH3:21])[CH3:22])[NH:15]2)=[CH:10][C:9]=1[N+:11]([O-:13])=[O:12])([CH3:26])([CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 59129414N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide

Product 1

HCID 534216126-Tert-butoxy-2-tert-butyl-5-nitro-1H-indoleYield 21.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide (500 mg, 1.63 mmol) and t-BuOK (0.37 g, 3.26 mmol) in DMF (10 mL) was heated at 70° C. for 2 h. The mixture was poured into water and then extracted with EtOAc (50 mL×3). The combined extracts were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to give 6-tert-butoxy-2-tert-butyl-5-nitro-1H-indole (100 mg, 21%). 1H-NMR (300 MHz, DMSO-d6) δ 11.35 (brs, 1H), 7.99 (s, 1H), 7.08 (s, 1H), 6.25 (s, 1H), 1.34 (s, 9H), 1.30 (s, 9H).

Workup

  1. extractionextracted with EtOAc (50 mL×3)
  2. washThe combined extracts were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d63c64bea2634aeca6d2c89daf404ce4
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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