Potassium Phosphate, Tribasic → tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)-1-methylethyl]carbamate

HRID 1026204ノート

反応式

HRID 1026204 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]3[N:10]=[CH:11][O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.Br[C:16]1[N:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])=[CH:18][CH:17]=1.C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN1CCCC1=O>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]3[N:10]=[C:11]([C:16]4[N:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])=[CH:18][CH:17]=4)[O:12][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 677784246-(Cyclopropylmethoxy)-1,3-benzoxazoleHCID 86666261tert-butyl {(1S)-2-[(6-bromopyridin-3-yl)oxy]-1-methylethyl}carbamate

生成物 1

HCID 86666262tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)-1-methylethyl]carbamate収率 34.4%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
125 °C

実験手順

A mixture of 6-(cyclopropylmethoxy)-1,3-benzoxazole (500 mg), tert-butyl {(1S)-2-[(6-bromopyridin-3-yl)oxy]-1-methylethyl}carbamate (1.31 g), palladium(II) acetate (29 mg), butyldi(1-adamantyl)phosphine (93 mg), tripotassium phosphate (1.12 g) and N-methylpyrrolidone (12 mL) was stirred under an argon atmosphere at 125° C. for 15 hr. The reaction mixture was allowed to cool to room temperature, and filtered through celite. The filtrate was diluted with ethyl acetate and water, and the organic layer was separated. The combined 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 (400 mg).

後処理

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

出典と根拠

ORDレコード
ord-cf87df726f16492d95136896b423f8ec
出典データセット
uspto-grants-2014_05
特許番号
US08729102B2

反応ノート

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