Water → Benzyl 2-(1-benzyl-3-cyclopropylindazol-6-yloxy)ethylcarbamate

HRID 1873971Notes

Reaction equation

HRID 1873971 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=2)[C:24]([CH:32]2[CH2:34][CH2:33]2)=[N:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:29]=2)[C:24]([CH:32]2[CH2:33][CH2:34]2)=[N:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 278694benzyl N-(2-bromoethyl)carbamateHCID 1358699421-Benzyl-3-cyclopropylindazol-6-ol

Product 1

HCID 59370774Benzyl 2-(1-benzyl-3-cyclopropylindazol-6-yloxy)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl 2-bromoethylcarbamate (1.0563 g) which can be prepared according to the method described in Reference example 40, etc. was dissolved in dehydrated DMF (5 mL), added with 1-benzyl-3-cyclopropylindazol-6-ol (533.4 mg) which can be prepared according to the method described in Reference example 3, etc. and potassium carbonate (879.1 mg), and stirred overnight at 50° C. under nitrogen atmosphere. After cooling to room temperature, the reaction solution was added to water and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over sodium sulfate. After the solvent was evaporated under reduced pressure, the resulting reside was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=81:19→60:40) to obtain the title compound as a crude product (508.2 mg).

Workup

  1. customcan be prepared
  2. temperatureAfter cooling to room temperature
  3. washThe organic layer was washed twice with water and once with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe resulting reside was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=81:19→60:40)

Sources & evidence

ORD record
ord-cfac119e45ad4e9f8922ddc737d836a9
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

Loading…