1-Methyl-1H-indole-4-carbaldehyde → alpha-(2-methoxyphenyl)-1-methyl-1H-indol-4-methanol

HRID 1533989Notes

Reaction equation

HRID 1533989 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:11]=[O:12])[C:5]=2[CH:4]=[CH:3]1.[Mg].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]>O1CCCC1>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:11]([C:6]1[C:5]2[CH:4]=[CH:3][N:2]([CH3:1])[C:10]=2[CH:9]=[CH:8][CH:7]=1)[OH:12]

Participants

4

Reactant 2

HCID 172211111-Methyl-1H-indole-4-carbaldehydeHCID 668624672-Bromo anisole magnesium

Product 1

HCID 19800111alpha-(2-methoxyphenyl)-1-methyl-1H-indol-4-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure of Step B of Example 1, 36.8 g of the product of Step A and 104 ml of a solution of 2-bromo anisole magnesium compound in tetrahydrofuran titrating 1.94N were reacted. Extraction was carried out with ethyl acetate and the extracts were washed with salt water and brought to dryness. The residue was chromatographed on silica (eluant: methylene chloride) to obtain 46.5 g of the expected product melting at 95° C.

Workup

  1. customwere reacted
  2. extractionExtraction
  3. washthe extracts were washed with salt water
  4. customThe residue was chromatographed on silica (eluant: methylene chloride)

Sources & evidence

ORD record
ord-d6d471eee1f34576a19414009b9c5325
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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