HCID 15678805, compound → HCID 15678806, compound

HRID 1090204Notes

Reaction equation

HRID 1090204 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:7]2[C:12]([C:13]=1[CH3:14])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=O.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:6]2[C:7]3[C:12](=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3)[C:13]([CH3:14])=[C:5]2[CH2:3][OH:2])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 15678805HCID 15678805, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15678806HCID 15678806, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.50 g 1-(4-chlorobenzyl)-3-methyl-5-methoxy-1H-indole-2-carboxylate methyl ester was dissolved in 50 ml dry THF. Diisobutyl aluminum hydride (1.5M) in THF (2 equivalents) was added at -78° C. The reaction was stirred for 16 hrs., allowed to reach room temperature and quenched with NH4Cl (aq.). The organic phase was separated, dried (Na2SO4) and evaporated to produce 1.32 g of product which was purified on column chromatography to yield the title compound of Step 2.

Workup

  1. customto reach room temperature
  2. customquenched with NH4Cl (aq.)
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-17c79383a96d4efbb80285fee02e3bc5
Source dataset
uspto-grants-1992_01
Patent number
US05081145

Reaction notes

Loading…