Hydrochloric Acid → HCID 10637623, compound

HRID 2292751Notes

Reaction equation

HRID 2292751 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[N:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]=1[CH3:22].B(Br)(Br)Br.COC1C=C2C(=CC=1)N(CC1C=CC=CC=1)C(C)=C2CC(O)=O.Cl>C(Cl)Cl.CCO>[OH:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]([CH3:22])=[C:5]2[CH2:4][C:3]([OH:23])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13722-(1-benzyl-5-methoxy-2-methylindol-3-yl)acetic acidHCID 25134Boron tribromideHCID 10614831HCID 10614831, compound

Product 1

HCID 10637623HCID 10637623, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester. Three mL (30 mmol) of BBr3 was added to 3.1 g (10 mmol) of 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid in 250 mL of CH2Cl2 and the mixture stirred for 17 hours. After stirring with 1N HCl, some EtOH was added, the organic layer separated, washed with a saturated NaCl solution, dried and concentrated at reduced pressure to give 2.95 g (100% yield) of crude 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid. A methanol solution of 1.7 g of the material was treated with sulfuric acid as described in Part A to give after silica gel chromatography (30% ether/hexane→60% ether/hexane) 1.5 g of 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester.

Workup

  1. customthe organic layer separated
  2. washwashed with a saturated NaCl solution
  3. customdried
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-8de9d3aa98654de187ec7c2d9c1e0c50
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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