Hydrochloric Acid → HCID 86731349, compound

HRID 2277271Notes

Reaction equation

HRID 2277271 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]2[O:13][C:14]3[CH:20]=[C:19]([O:21][CH2:22][C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:5]=[C:6]([F:11])[C:7]=1[O:8][CH2:9][CH3:10].C([Sn](CCCC)(CCCC)[C:34]([O:36]CC)=[CH2:35])CCC.Cl.C(=O)([O-])O.[Na+]>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.C1(C)C=CC=CC=1>[C:34]([C:2]1[CH:3]=[C:4]([C:12]2[O:13][C:14]3[CH:20]=[C:19]([O:21][CH2:22][C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:5]=[C:6]([F:11])[C:7]=1[O:8][CH2:9][CH3:10])(=[O:36])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86731350HCID 86731350, compound

Product 1

HCID 86731349HCID 86731349, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of N-((2S)-1-((2-(3-bromo-4-ethoxy-5-fluorophenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide (1.50 g) and toluene (10 mL) were added tributyl(1-ethoxyvinyl)stannane (2.25 mL) and tetrakis(triphenylphosphine)palladium(0) (192 mg), and the mixture was stirred at 110° C. for 5 hr under an argon atmosphere. To the reaction mixture was added 0.5N hydrochloric acid, and the mixture was stirred at room temperature for 1 hr, neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The obtained solid was washed with diethyl ether-hexane to give the title compound (1.22 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. washThe obtained solid was washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-6c616247e1df40f88ca3620a58dcf750
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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