Water → HCID 86674214, compound

HRID 2167151Notes

Reaction equation

HRID 2167151 reaction equation
Cl[C:2]1[C:3]([CH:22]=[O:23])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:24][C:25]1(C)[C:29](C)(C)OB(C(C)=C)O1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.O>O1CCOCC1.CC(O)=O.CC(O)=O.[Pd]>[CH:22]([C:3]1[C:2]([C:25]([CH3:29])=[CH2:24])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=1)=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86674213HCID 86674213, compound

Product 1

HCID 86674214HCID 86674214, compound

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 3′-chloro-2′-formyl-5′-(trifluoromethyl)-[1,1′-biphenyl]-4-carboxylate (430 mg, 1.3 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.59 mL, 3.1 mmol), S-PHOS (103 mg, 0.3 mmol), Pd(Oac)2 (28 mg, 0.1 mmol) and K3PO4hydrate (1.3 g, 6.3 mmol) were dissolved in 1,4-dioxane (5 mL) and water (0.3 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature and filtered through CELITE. The filtrate was diluted EtOAc, washed with water and saturated aqueous NaHCO3, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. filtrationfiltered through CELITE
  2. washwashed with water and saturated aqueous NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-12f2bf923f66403d82fbb06d77a9adea
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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