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

HRID 2305590Notes

Reaction equation

HRID 2305590 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-971703a055824de9b6518988027451b4
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

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