Potassium Phosphate, Tribasic → HCID 58464728, compound

HRID 2089406Notes

Reaction equation

HRID 2089406 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:20])[C:5]([F:19])=[C:6]([B:8]2[O:15][C:14](=[O:16])[CH2:13][N:12]([CH3:17])[CH2:11][C:10](=[O:18])[O:9]2)[CH:7]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:21]1([C:2]2[CH:3]=[C:4]([CH3:20])[C:5]([F:19])=[C:6]([B:8]3[O:15][C:14](=[O:16])[CH2:13][N:12]([CH3:17])[CH2:11][C:10](=[O:18])[O:9]3)[CH:7]=2)[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 58464908HCID 58464908, compound

Product 1

HCID 58464728HCID 58464728, compoundYield 60.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave reaction vessel equipped with stir bar was charged 2-(5-bromo-2-fluoro-3-methylphenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (300 mg, 0.9 mmol), cyclopropylboronic acid (220 mg, 2.6 mmol), palladium acetate (14 mg, 0.06 mmol), S-Phos (50 mg, 0.12 mmol) and potassium phosphate (560 mg, 2.6 mmol). Degassed toluene (15 mL) was added. The reaction was heated under microwave at 120° C. for 15 min. LCMS indicated completion of the reaction. The mixture was diluted with acetonitrile and filtered through a pad of Celite and washed with copious amount of acetonitrile. The filtrate was concentrated in vacuo and the residue was absorbed on Celite from an acetone solution. The resulting powder was subjected to Isco flash chromatography eluted with 0 to 70% acetonitrile in ether to give a light yellow oil, 2-(5-cyclopropyl-2-fluoro-3-methylphenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (167 mg, 60%).

Workup

  1. customIn a microwave reaction vessel
  2. customequipped
  3. customcompletion of the reaction
  4. filtrationfiltered through a pad of Celite
  5. washwashed with copious amount of acetonitrile
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was absorbed on Celite from an acetone solution
  8. washeluted with 0 to 70% acetonitrile in ether

Sources & evidence

ORD record
ord-3f852eab04204d64bfef420c077d708f
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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