Potassium Carbonate → HCID 84663037, compound

HRID 1685574Notes

Reaction equation

HRID 1685574 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]([O:21]C(C)(C)C)=[O:20]>CC#N>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][CH2:18][C:19]([OH:21])=[O:20])[CH:10]=2)[CH:6]=[CH:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 5245086-Hydroxyindole

Product 1

HCID 84663037HCID 84663037, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Hydroxyindole (1.0 g, 7.51 mmol) in degassed MeCN (10 mL) was added K2CO3 (1.14 g, 8.26 mmol) followed by tert-butyl bromoacetate (1.16 g, 8.26 mmol) and the reaction mixture was stirred for 20 hours under N2. The precipitate was filtered off and the solvent was removed in vacuo to give (1-H-indole-6-yloxy)-acetic acid. This was converted to [1-Cyclopropylmethyl-3-(thiazol-2-ylcarbamoyl)-1H-indol-6-yloxy]-acetic acid tert-butyl ester following general procedure (A). [1-Cyclopropylmethyl-3-(thiazol-2-ylcarbamoyl)-1H-indol-6-yloxy]-acetic acid was obtained by treating the intermediate with TFA-DCM (1:1) (2 mL) for 90 min before the solvent was removed in vacuo.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8ff6ba0031134bdda6b80bf33c2aa64a
Source dataset
uspto-grants-2012_04
Patent number
US08148413B2

Reaction notes

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