Potassium Phosphate, Tribasic → HCID 71239958, compound

HRID 1753765Notes

Reaction equation

HRID 1753765 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[C:20](B2OC(C)(C)C(C)(C)O2)=[C:19]([CH3:30])[CH:18]=[CH:17][N:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C>CC(O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][O:14][C:15]1[C:20]([C:2]2[CH:7]=[C:6]([C:8]3[O:12][CH:11]=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[C:19]([CH3:30])[CH:18]=[CH:17][N:16]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 712410112-Methoxy-4-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86724050HCID 86724050, compound

Product 1

HCID 71239958HCID 71239958, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

An oven-dried flask under argon was charged with the 2-bromo-4-oxazol-5-yl-pyridine (Intermediate II-c, 461 mg, 2.07 mmol), 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine V-d (510 mg, 2.07 mmol), K3PO4 (2.82 g, 13.3 mmol), Pd(OAc)2 (51 mg, 0.225 mmol), Davephos (89 mg, 0.225 mmol) in iPrOH (5 mL) and water (3 mL). After 40 min at 100° C., the mixture was cooled to room temperature, diluted with water and extracted with EtOAc then washed with brine. The organics were dried (MgSO4), filtered and evaporated before purification by column chromatography (SiO2, 30% to 100% EtOAc in cyclohexane) to afford the desired product V-e as an off-white solid (240 mg, 43%). 1H NMR (300 MHz, CDCl3) δ 8.78 (d, J=4.8 Hz, 1H), 8.10 (d, J=4.8 Hz, 1H), 8.01 (s, 1H), 7.59 (d, J=4.9 Hz, 2H), 7.51 (d, J=4.9 Hz, 1H), 6.86 (d, J=4.9 Hz, 1H), 3.88 (s, 3H), 2.16 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washthen washed with brine
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated before purification by column chromatography (SiO2, 30% to 100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-24cdc4025f72497e8ae30c338f5abba6
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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