Sodium Carbonate → HCID 86681453, compound

HRID 339957Notes

Reaction equation

HRID 339957 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:25])[NH:13][C@@H:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)[CH2:15][OH:16])([CH3:10])([CH3:9])[CH3:8].[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>O.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>[OH:16][CH2:15][C@@H:14]([NH:13][C:12](=[O:25])[O:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:30]2[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=2)[CH:19]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58666623468740-94-52×

Product 1

HCID 86681453HCID 86681453, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

To 0.7 M potassium carbonate in water was added tert-butyl[(1S)-1-(3-bromobenzyl)-2-hydroxyethyl]carbamate [prepared according to Intermediate 15, Step A] (1.00 g, 3.03 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.82 g, 3.9 mmol) and 1,4-dioxane (26 mL, 340 mmol) and 2.0 M sodium carbonate in water (6.0 mL, 12 mmol). The mixture was flushed with nitrogen for 10 min. To the mixture was then added tetrakis(triphenylphosphine)palladium(0) (0.17 g, 0.15 mmol) and the mixture was heated at 100° C. for 30 min. The resulting mixture was purified on 40 g silica gel, 0-100% EtOAc in hexanes, and the pure fractions were combined, and solvent removed under vacuum to give 0.45 g of white solid. LC-MS found: 332.2 (m+1).

Workup

  1. customThe mixture was flushed with nitrogen for 10 min
  2. customThe resulting mixture was purified on 40 g silica gel, 0-100% EtOAc in hexanes
  3. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-69b87962d4e34dc698b90c98f1f93848
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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