HCID 90420412, compound → HCID 90420305, compound

HRID 1771861Notes

Reaction equation

HRID 1771861 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:21]([C:23]3[S:24][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[N:27]=3)[CH3:22])=[C:9]([CH:11]([OH:20])C(C3C=CC=CC=3)O)[N:10]=2)[CH:7]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:21]([C:23]3[S:24][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[N:27]=3)[CH3:22])=[C:9]([CH:11]=[O:20])[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 90420412HCID 90420412, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 90420305HCID 90420305, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-4 °C

Procedure

A solution of 1-(6-bromo-3-((4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)imidazo[1,2-a]pyridin-2-yl)-2-phenylethane-1,2-diol (Gen-5-ab) (10.8 g, 20 mmol, 1 eq.) in DCM (500 mL) was cooled to −4° C. Lead tetraacetate (dried before use, 13.3 g, 30 mmol, 1.5 eq.) was added and stirred at −4° C. for 0.5 h. The reaction was quenched by addition of water (500 mL). The mixture was filtered and the layers in the filtrate were separated. The aqueous layer was extracted with DCM (2×200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel (elution with heptane/EtOAc 100/0 to 50/50) to give an additional amount of Intermediate Gen-5-q 6-bromo-3-((4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)imidazo[1,2-a]pyridine-2-carbaldehyde.

Workup

  1. customThe reaction was quenched by addition of water (500 mL)
  2. filtrationThe mixture was filtered
  3. customthe layers in the filtrate were separated
  4. extractionThe aqueous layer was extracted with DCM (2×200 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel (elution with heptane/EtOAc 100/0 to 50/50)

Sources & evidence

ORD record
ord-3e9d83e1ff874bd6a2b13434b99c57c6
Source dataset
uspto-grants-2016_02
Patent number
US09249141B2

Reaction notes

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