Iodine → HCID 67003444, compound

HRID 2362620Notes

Reaction equation

HRID 2362620 reaction equation
[Cl:1][C:2]1[C:3]([C:21]2[S:25][C:24]([C:26]3([O:30][CH2:31][O:32][CH3:33])[CH2:29][CH2:28][CH2:27]3)=[N:23][CH:22]=2)=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[I:42]I>O1CCCC1>[Cl:1][C:2]1[C:3]([C:21]2[S:25][C:24]([C:26]3([O:30][CH2:31][O:32][CH3:33])[CH2:29][CH2:28][CH2:27]3)=[N:23][CH:22]=2)=[C:4]2[CH:10]=[C:9]([I:42])[N:8]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=3)(=[O:12])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 67003633HCID 67003633, compound

Product 1

HCID 67003444HCID 67003444, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of 5-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 1E) (5.0 g, 9.92 mmol) in tetrahydrofuran (50 mL) was added a solution of lithium diisopropylamide (13.9 mmol) in tetrahydrofuran (15 mL). The reaction was stirred at −78° C. for 1 hour, and a solution of iodine (3.52 g, 13.89 mmol) in tetrahydrofuran (10 mL) was added. The cold bath was removed, and, after 15 minutes, the reaction was quenched by the addition of saturated aqueous sodium thiosulfate and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 30% ethyl acetate in hexane, to give the title compound. MS ESI(+) m/z 586 [M+H]+;

Workup

  1. customThe cold bath was removed
  2. waitafter 15 minutes
  3. customthe reaction was quenched by the addition of saturated aqueous sodium thiosulfate and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  6. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel
  10. washeluting with a gradient of 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-59e379a29eab4fbb99806da4d963c1d3
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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