Hydrochloric Acid → Methyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetate

HRID 1683975Notes

Reaction equation

HRID 1683975 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]#N)[CH2:20][CH2:19]3)=[C:8]2[CH3:24])=[CH:4][CH:3]=1.Cl.[OH-:28].[Na+].[CH3:30][OH:31]>>[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([O:31][CH3:30])=[O:28])[CH2:20][CH2:19]3)=[C:8]2[CH3:24])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 19041631[1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)-cyclopropyl]acetonitrile

Product 1

HCID 53800337Methyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetate

Procedure

To a -5° C. suspension of the nitrile from Step 6 (1.59 g, 3.88 mmol) in 15 mL methanol was added HCl gas to give a saturated solution. The mixture was then heated to reflux overnight, cooled and poured into ice water. The mixture was adjusted to pH 10 with 2.0N NaOH, and then extracted with ethyl acetate. The organic extracts were washed with saturated NaHCO3 and brine, dried over MgSO4 and evaporated. Purification by flash chromatography (15% ethyl acetate/hexanes) provided 1.63 g of the title compound.

Workup

  1. customto give a saturated solution
  2. temperatureThe mixture was then heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. washThe organic extracts were washed with saturated NaHCO3 and brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customPurification by flash chromatography (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cce9861baa1b4808b4ef87dc0b4839b3
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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