Potassium Carbonate → HCID 71087598, compound

HRID 927410Notes

Reaction equation

HRID 927410 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[O:11]1[CH2:16][CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:11]1[CH2:12][CH:13]=[C:14]([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5939196-Bromopyridine-2-carboxylic acidHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Product 1

HCID 71087598HCID 71087598, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Procedure

Under an atmosphere of nitrogen, a solution of 6-bromo-pyridine-2-carboxylic acid (CAN: 21190-87-4, 1 g, 4.9 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Example 9-d, 1.1 g, 5.4 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 0.08 g, 0.1 mmol) and potassium carbonate (1.37 g, 10 mmol) in water (50 mL) was stirred for 24 h at 100° C. The reaction mixture was extracted with ethyl acetate (50 mL), the pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (6×50 mL), dried over anhydrous sodium sulfate and evaporated. The residue was purified by prep-HPLC to yield the title compound (0.3 g, 1.5 mmol, 29.5%) as white solid; MS (EI): m/e=206.1 [M+H]+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (50 mL)
  2. additionthe pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid
  3. extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with brine (6×50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-8863659586164dd5bc0c6b2ad2e6e8f4
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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