Carbon Dioxide → HCID 24990706, compound

HRID 659148Notes

Reaction equation

HRID 659148 reaction equation
Br[C:2]1[S:6][C:5]2=[N:7][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[CH:9][N:4]2[CH:3]=1.C([Li])CCC.[C:22](=[O:24])=[O:23]>C1COCC1.CCCCCC>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[N:7]=[C:5]3[N:4]([CH:9]=2)[CH:3]=[C:2]([C:22]([OH:24])=[O:23])[S:6]3)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 249907052-Bromo-6-(4-fluoro-phenyl)-imidazo[2,1-b]thiazoleHCID 178418339Butyllithium

Product 1

HCID 24990706HCID 24990706, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-bromo-6-(4-fluoro-phenyl)-imidazo[2,1-b]thiazole (example 22, 100 mg, 0.336 mmol) in 5 ml THF were added 200 μl butyllithium (2.5 M) in hexane at −60° C. The mixture was stirred for 10 min, solid carbon dioxide was added and the mixture was allowed to warm at RT. The solution was quenched with methanol and water, acidified and extracted with ethyl acetate. The organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 9 mg (10%) of the desired product. MS: M+H+=263.03.

Workup

  1. customThe solution was quenched with methanol and water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-88a9cca937c04a05b15e47bdb2f73249
Source dataset
uspto-grants-2011_12
Patent number
US08080569B2

Reaction notes

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