Water → 7-Bromo-5-methoxyindoline

HRID 1066758Notes

Reaction equation

HRID 1066758 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:18][CH3:19])=[CH:14][C:15]=2[Br:17])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC.O.[OH-].[Na+]>CO.CCOCC>[Br:17][C:15]1[CH:14]=[C:13]([O:18][CH3:19])[CH:12]=[C:11]2[C:16]=1[NH:8][CH2:9][CH2:10]2

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10953452Ether hydrochlorideHCID 186292191h-Indole-1-carboxylic acid,7-bromo-2,3-dihydro-5-methoxy-,1,1-dimethylethyl ester

Product 1

HCID 184528187-Bromo-5-methoxyindolineYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

To 1-(tert-butoxycarbonyl)-7-bromo-5-methoxyindoline (1.16 g) in methanol (28 mL) was added HCl/ether (1.0 M, 14.1 mL, 4 eq.). The reaction was heated at 55° C. for 4 hours and then cooled to room temperature. Water (25 mL) was added and the pH was adjusted to 9 with NaOH (1 N, aq.). The mixture was extrated with ether, which was washed with brine, dried over MgSO4, and concentrated to give 7-bromo-5-methoxyindoline (685 mg).

Workup

  1. temperaturecooled to room temperature
  2. washwas washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b642fc9e3104340befd9db225a6ebb6
Source dataset
uspto-grants-2001_06
Patent number
US06245769B1

Reaction notes

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