Nitrogen → HCID 84663037, compound

HRID 1159140Notes

Reaction equation

HRID 1159140 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].N#N>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

6

Reactant 4

HCID 947NitrogenHCID 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 hous 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 follwing 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-a5abf13e46b2414889e54f40dd9a031f
Source dataset
uspto-grants-2010_10
Patent number
US07812043B2

Reaction notes

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