Hydrochloric Acid → HCID 10637623, compound

HRID 1901791Notes

Reaction equation

HRID 1901791 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 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 saturated NaCl solution
  3. customdried
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-73696bf0578342ec805934ce3454f9e8
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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