Bicarbonate Ion → HCID 86659279, compound

HRID 2362626Notes

Reaction equation

HRID 2362626 reaction equation
[Cl: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.[CH:32]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)=[O:33].C(=O)(O)[O-]>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>[Cl: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]([C:37]3[CH:38]=[CH:39][C:34]([CH:32]=[O:33])=[CH:35][CH:36]=3)[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

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 5910734-Formylphenylboronic AcidHCID 67003374HCID 67003374, compound

Product 1

HCID 86659279HCID 86659279, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred ambient solution of 1-(5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 8A) (2.85 g, 4.86 mmol) and 4-formylphenylboronic acid (1.094 g, 7.30 mmol) in N,N-dimethylformamide (36.5 ml) was added saturated aqueous bicarbonate solution (12.16 ml) followed by bis(triphenylphosphine)palladium dichloride (0.239 g, 0.341 mmol). The mixture was heated to 70° C. for 2 hours, cooled to room temperature, and quenched by the addition of water and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate. 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 70% ethyl acetate in hexane, to afford the title compound. MS ESI(+) m/z 564.5 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. customquenched by the addition of water and ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 0 to 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ebd786d92d0e456f8ad57109c320b7cd
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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