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

HRID 2277155ノート

反応式

HRID 2277155 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
125 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-554c111a0084499bb69015d27a3bcb54
出典データセット
uspto-grants-2015_09
特許番号
US09133129B2

反応ノート

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