Potassium Carbonate → HCID 58494092, compound

HRID 1942696Notes

Reaction equation

HRID 1942696 reaction equation
[CH2:1]([C:3]1[C:8]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH:18]1[CH2:21][NH:20][CH2:19]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(#N)C>[CH2:1]([C:3]1[C:8]([B:9]2[O:10][C:11]([CH3:16])([CH3:17])[C:12]([CH3:14])([CH3:15])[O:13]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH:18]1[CH2:21][N:20]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:19]1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 58494064HCID 58494064, compound

Product 1

HCID 58494092HCID 58494092, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-[2-ethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-azetidine (D131) (295 mg, 0.735 mmol) in Acetonitrile (10 mL) was added potassium carbonate (305 mg, 2.206 mmol) and ethyl 4-bromobutanoate (0.158 mL, 1.103 mmol). The reaction solution was heated to 60° C. overnight. The solvent was removed in vacuo and the residue was diluted with ethyl acetate, washed with water, dried and concentrated to afford ethyl 4-{3-[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-azetidinyl}butanoate (D132) (295 mg) as an oil. MS (ES): C23H36BNO4 requires 401.3. found 402.3 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2684186275db4e9b953298469b0faf6b
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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