Ethyl Acetate → HCID 66611924, compound

HRID 2204699Notes

Reaction equation

HRID 2204699 reaction equation
Br[C:2]1[C:3]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[CH3:31][N:32]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[N:33]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:29][N:28]([CH3:30])[C:26]([C:3]1[C:2]([C:35]2[CH:34]=[N:33][N:32]([CH3:31])[CH:36]=2)=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:4]=1)=[O:27]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 66611580HCID 66611580, compound

Product 1

HCID 66611924HCID 66611924, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
125 °C

Procedure

Phenylmethyl 5-bromo-4-[(dimethylamino)carbonyl]-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 39; 195 mg) was redissolved in 1,2-dimethoxyethane (5 ml) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (103 mg, 0.49 mmol), tripotassium phosphate (168 mg, 0.79 mmol) and Pd(Ph3P)4 (34.3 mg, 0.03 mmol) were added. The mixture was heated at 125° C. for 50 minutes. Ethyl acetate (10 ml) and water (10 ml) were added. The organic layer was separated and dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane-10% 2M NH3 in CH3OH/dichloromethane) gave the title compound as a brown gum. 195 mg.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customPurification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane-10% 2M NH3 in CH3OH/dichloromethane)

Sources & evidence

ORD record
ord-d6ab26e597a04bee9412cd5e44346441
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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