Nitromethane → 6-Bromo-1-methyl-2-(2-nitroethenyl)-1H-indole

HRID 2365418Notes

Reaction equation

HRID 2365418 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:12]=O)[N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH3:14][N+:15]([O-:17])=[O:16]>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:12]=[CH:14][N+:15]([O-:17])=[O:16])[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6375NitromethaneHCID 751762556-Bromo-1-methylindole-2-carbaldehyde

Product 1

HCID 679692016-Bromo-1-methyl-2-(2-nitroethenyl)-1H-indoleYield 99%

Procedure

A solution of 6-bromo-1-methyl-1H-indole-2-carbaldehyde (422 mg, 1.77 mmol) and NH4OAc (137 mg, 1.77 mmol) in MeNO2 (10.0 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature and partitioned between water and EtOAc. The aqueous phase was separated and extracted with EtOAc (3×). The organic extracts were dried over Na2SO4, filtered and concentrated to give title compound (490 mg, 99%) as an orange solid: 1H NMR (500 MHz, CDCl3) δ 8.12 (d, J=13.0 Hz, 1H), 7.67 (d, J=13.5 Hz, 1H), 7.53 (s, 1H), 7.50 (d, J=8.5 Hz, 1H), 7.26 (dd, J=8.5, 1.5 Hz, 1H), 7.05 (s, 1H), 3.84 (s, 3H).

Workup

  1. temperatureto reflux for 2 h
  2. custompartitioned between water and EtOAc
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-79450590c6b549528f7544d8acbabc51
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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