HCID 90420412, compound → HCID 90420305, compound

HRID 880606Notes

Reaction equation

HRID 880606 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-30b50439c8f54a788e1e02e40e049f7e
Source dataset
uspto-grants-2015_03
Patent number
US08993590B2

Reaction notes

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