Carbonate Ion → HCID 67384820, compound

HRID 1471940Notes

Reaction equation

HRID 1471940 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 IonHCID 24408BromineHCID 67385068HCID 67385068, compound

Product 1

HCID 67384820HCID 67384820, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-5-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)-3-phenyl-1H-pyrazole (2.3 g, 8.45 mmol) and MP-carbonate (26 g, 84.5 mmol) in CH2Cl2 (100 mL), was added bromine (1.350 g, 8.45 mmol) dropwise at 0° C. After stirring for 1 h, MP-carbonate was filtered off and washed with CH2Cl2. The combined organic layer was poured into water, extracted with CH2Cl2, dried over MgSO4, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography to give the title compound (2.81 g) as an oil. LCMS m/z=351.2 [M+H]+.

Workup

  1. filtrationMP-carbonate was filtered off
  2. washwashed with CH2Cl2
  3. additionThe combined organic layer was poured into water
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-28cd95bfa9fc4a07b66c330799991564
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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