HCID 67002664, compound → HCID 67003885, compound

HRID 2362730Notes

Reaction equation

HRID 2362730 reaction equation
[F:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([OH:31])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:37]1[S:41][C:40]([C:42]23[CH2:49][N:46]([CH2:47][CH2:48]2)[CH2:45][CH2:44][O:43]3)=[N:39][CH:38]=1)CCC>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:46]12[CH2:49][C:42]([C:40]3[S:41][C:37]([C:9]4[N:8]([S:12]([C:15]5[CH:16]=[CH:17][C:18]([CH3:19])=[CH:20][CH:21]=5)(=[O:14])=[O:13])[C:5]5=[N:6][CH:7]=[C:2]([F:1])[C:3]([C:22]6[S:26][C:25]([C:27]7([OH:31])[CH2:28][CH2:29][CH2:30]7)=[N:24][CH:23]=6)=[C:4]5[CH:10]=4)=[CH:38][N:39]=3)([CH2:48][CH2:47]1)[O:43][CH2:44][CH2:45]2

Participants

5

Reactant 2

HCID 67002664HCID 67002664, compoundHCID 670034821-(5-(5-fluoro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol

Product 1

HCID 67003885HCID 67003885, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(5-(5-fluoro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (150 mg, 0.263 mmol), 5-(5-(tributylstannyl)thiazol-2-yl)-4-oxa-1-azabicyclo[3.2.1]octane (192 mg, 0.395 mmol), and bis(triphenylphosphine)palladium dichloride (0.013 g, 0.025 mmol) in N,N-dimethylformamide (1.8 mL) was heated to 70° C. for 2 hours. The reaction was quenched by the addition of an aqueous potassium fluoride solution (1.0 g in 2.5 mL water) and ethyl acetate (5 mL). The mixture was stirred vigorously overnight and was then filtered through diatomaceous earth, eluting with ethyl acetate. The layers were separated, and the organic layer was washed with aqueous saturated sodium bicarbonate and water. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 638.2 [M+H]+.

Workup

  1. customThe reaction was quenched by the addition of an aqueous potassium fluoride solution (1.0 g in 2.5 mL water) and ethyl acetate (5 mL)
  2. filtrationwas then filtered through diatomaceous earth
  3. washeluting with ethyl acetate
  4. customThe layers were separated
  5. washthe organic layer was washed with aqueous saturated sodium bicarbonate and water
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-337568d2dc714ddb804a3cfac8259c97
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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