Sodium Carbonate → HCID 136063621, compound

HRID 1692262Notes

Reaction equation

HRID 1692262 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:3]=1.Cl[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:20]=2)[CH:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 1516418tert-butyl N-(4-chloropyridin-2-yl)carbamateHCID 567377034-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 136063621HCID 136063621, compound

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (Preparation 212, 0.082 g, 0.000386 mol), tert-butyl (4-chloropyridin-2-yl)carbamate (0.0588 g, 0.000257 mol), anhydrous sodium carbonate (0.070 g, 0.000660 mol) and palladium (0) tetrakis(triphenylphosphine) (0.029 mg, 0.000025 mol) were suspended in 1,4-dioxane (3.0 ml) and water (1.0 ml). The suspension was stirred at 85° C. for 16 hours before cooling to room temperature. The reaction was diluted with ethyl acetate (10 ml) and organic phase was washed with saturated aqueous sodium bicarbonate solution (2×10.0 ml), dried over sodium sulphate, filtered and concentrated in vacuo. Purification by ISCO™ (12 g SiO2) eluting with ethyl acetate:heptane (gradient 0:1 to 3:7, by volume) afforded the title compound as a solid, 41 mg, 54%.

Workup

  1. temperaturebefore cooling to room temperature
  2. washwas washed with saturated aqueous sodium bicarbonate solution (2×10.0 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by ISCO™ (12 g SiO2)
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-26e8089f01d24096ab1dfd4528099c58
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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