Potassium Phosphate, Tribasic → tert-butyl ((2S)-1-((2-(5-(cyclopropylmethoxy)pyridin-2-yl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate

HRID 2277155Notes

Reaction equation

HRID 2277155 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([O:10][CH2:11][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)=[CH:25][N:24]=1.C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN1CCCC1=O>[CH:31]1([CH2:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([C:2]3[O:1][C:5]4[CH:6]=[C:7]([O:10][CH2:11][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:8]=[CH:9][C:4]=4[N:3]=3)=[N:24][CH:25]=2)[CH2:32][CH2:33]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 578217962-Bromo-5-(cyclopropylmethoxy)pyridineHCID 86731209HCID 86731209, compound

Product 1

HCID 86731208tert-butyl ((2S)-1-((2-(5-(cyclopropylmethoxy)pyridin-2-yl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamateYield 47.6%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of tert-butyl ((2S)-1-(1,3-benzoxazol-6-yloxy)propan-2-yl)carbamate (516 mg), 2-bromo-5-(cyclopropylmethoxy)pyridine (604 mg), palladium(II) acetate (19.8 mg), butyldi(1-adamantyl)phosphine (63.3 mg), tripotassium phosphate (749 mg) and N-methylpyrrolidone (7 mL) was stirred at 125° C. for 15 hr under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (369 mg).

Workup

  1. temperatureto cool to room temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-554c111a0084499bb69015d27a3bcb54
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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