Aluminium lithium hydride → HCID 67969245, compound

HRID 2365419Notes

Reaction equation

HRID 2365419 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:12]=[CH:13][N+:14]([O-])=O)[N:8]2[CH3:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:12][CH2:13][NH2:14])[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 679692016-Bromo-1-methyl-2-(2-nitroethenyl)-1H-indole

Product 1

HCID 67969245HCID 67969245, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-1-methyl-2-(2-nitrovinyl)-1H-indole (871 mg, 3.10 mmol) in THF (60.0 mL) at 0° C. was added LiAlH4 (2.0 M in THF, 6.20 mL, 12.4 mmol) dropwise. The reaction mixture was allowed to warm to room temperature over 5 h and then quenched with water and 10% aqueous NaOH (20 mL) at 0° C. to form a precipitate which was filtered through filter paper. The filtrate was extracted with EtOAc. The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 90:10 to 20:80) gave the title compound (329 mg, 42%) as a brown oil: 1H NMR (500 MHz, CDCl3) δ 7.42 (s, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.17 (dd, J=8.5, 2.0 Hz, 1H), 6.27 (d, J=1.0 Hz, 1H), 3.65 (s, 3H), 3.08-3.55 (m, 2H), 2.92-2.87 (m, 2H).

Workup

  1. customquenched with water and 10% aqueous NaOH (20 mL) at 0° C.
  2. customto form a precipitate which
  3. filtrationwas filtered
  4. filtrationthrough filter paper
  5. extractionThe filtrate was extracted with EtOAc
  6. dry with materialThe extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 90:10 to 20:80)

Sources & evidence

ORD record
ord-02b489009e8d4bc8a63d0105ba3b0f2f
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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