Sodium Bicarbonate → HCID 22477391, compound

HRID 549082Notes

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9](OS(C(F)(F)F)(=O)=O)=[C:4]2[CH:3]=[CH:2]1.[CH3:18][C:19]1[C:23](B(O)O)=[C:22]([CH3:27])[O:21][N:20]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:18][C:19]1[C:23]([C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:1][CH:2]=[CH:3][C:4]=23)=[C:22]([CH3:27])[O:21][N:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of trifluoro-methanesulfonic acid-1H-pyrrolo[2,3-b]pyridin-4-yl ester [4.05 g, Reference Example 18(g)] and 3,5-dimethylisoxazole-4-boronic acid (2.31 g) in dimethylformamide (100 mL) was added tetrakis(triphenylphosphine)palladium[0] (0.1 g) and saturated sodium bicarbonate solution (30 mL). The resulting mixture was stirred at 110° C. for 5 hours. The reaction mixture was cooled and filtered through celite. The filtrate was evaporated to dryness and the residue partitioned between ethyl acetate (100 mL) and water (50 mL). The aqueous phase was extracted with ethyl acetate and the combined organic fractions were washed twice with brine (30 mL), then dried over magnesium sulfate and then evaporated to afford the title compound as an orange oil which was used immediately without further purification for the preparation of Reference Example 9(i).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered through celite
customThe filtrate was evaporated to dryness
customthe residue partitioned between ethyl acetate (100 mL) and water (50 mL)
extractionThe aqueous phase was extracted with ethyl acetate
washthe combined organic fractions were washed twice with brine (30 mL)
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-0d47d1c412f3487388d76a61357f8355
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943616B2

Reaction notes

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