Ethyl Acetate → HCID 11588178, compound

HRID 1189110Notes

Reaction equation

HRID 1189110 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([CH2:11][CH2:12][C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:7][C:6]=2[CH:5]=[C:4]([F:21])[CH:3]=1.C([O-])(O)=O.[Na+].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOC(C)=O>O1CCOCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:21][C:4]1[CH:3]=[C:2]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:10]2[O:9][C:8]([CH2:11][CH2:12][C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:7][C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 11595384HCID 11595384, compound

Product 1

HCID 11588178HCID 11588178, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-bromo-5-fluoro-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole (100 mg, 0.29 mmol, Example 82) in dioxane/aqueous saturated solution of NaHCO3 (1:1, 8 mL) were added Pd(PPh3)4 (33 mg, 29 μmol) and phenylboronic acid (53.0 mg, 0.43 mmol). The reaction mixture was stirred at 60° C. for 7 hours, then AcOEt and brine were added and the organic phase was discarded. The aqueous phase was extracted thrice with AcOEt. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 86 mg (0.25 mmol, 87%) of 5-fluoro-7-phenyl-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as an orange oil.

Workup

  1. extractionThe aqueous phase was extracted thrice with AcOEt
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-95e8c05d4487464d9333798cebafde25
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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