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

HRID 2277155노트

반응식

HRID 2277155 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
125 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-554c111a0084499bb69015d27a3bcb54
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133129B2

반응 노트

불러오는 중…