Carbonate Ion → HCID 67384825, compound

HRID 1471860Notes

Reaction equation

HRID 1471860 reaction equation
[CH3:1][C:2]1([CH3:20])[O:6][C@@H:5]([CH2:7][CH2:8][C:9]2[NH:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=2)[CH2:4][O:3]1.C(=O)([O-])[O-].[Br:25]Br>C(Cl)Cl>[Br:25][C:10]1[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][NH:13][C:9]=1[CH2:8][CH2:7][C@H:5]1[CH2:4][O:3][C:2]([CH3:20])([CH3:1])[O:6]1

Participants

5

Reactant 3

HCID 19660Carbonate Ion2×HCID 24408BromineHCID 67384746HCID 67384746, compound

Product 1

HCID 67384825HCID 67384825, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-5-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)-3-phenyl-1H-pyrazole (1.1 g, 4.04 mmol) and MP-carbonate in CH2Cl2 (50 mL) was added bromine (0.645 g, 4.04 mmol) dropwise at 0° C. After stirring for 1 h, MP-carbonate (12.4 g, 40.4 mmol) was filtered off and washed with CH2Cl2. The combined filtrate was poured into water, extracted with CH2Cl2, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as an oil (1.129 g). LCMS m/z=351.1 [M+H]+.

Workup

  1. washwashed with CH2Cl2
  2. additionThe combined filtrate was poured into water
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-759bcc56a8dd4459a7763a6b2cac8eb8
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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