Isopropanol → Isopropyl 3-methyl-1h-indole-2-carboxylate

HRID 967108Notes

Reaction equation

HRID 967108 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=O.[CH:19](O)(C)C>[Pd]>[CH3:3][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]([O:16][CH:17]([CH3:18])[CH3:19])=[O:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 5107764ethyl 3-formyl-1H-indole-2-carboxylate

Product 1

HCID 22311011Isopropyl 3-methyl-1h-indole-2-carboxylateYield 25%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Sodium borohydride (0.23 g) was added to a stirred solution of ethyl 3-formylindole-2-carboxylate (0.2 g) and 10% palladium on carbon (0.11 g) in isopropanol (45 ml). The solution was heated at reflux for 4 hours, cooled and filtered through Celite. The solution was partitioned between ethyl acetate and water. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-10% ethyl acetate as eluent to give the desired end product as a white solid (0.05 g, 25%); NMR δ (CD3SOCD3) 1.3 (d, 6H), 2.5 (s, 3H), 5.2 (m, 1H), 7.0 (m, 1H), 7.2 (m, 1H), 7.4 (m, 1H), 7.6 (d, 1H), 11.3 (bs, 1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. filtrationfiltered through Celite
  5. customThe solution was partitioned between ethyl acetate and water
  6. dry with materialCombined organic extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-4cd4e68d9b5e49c79c1d1f5d267ea6de
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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