Phenylboronic Acid → (R)-2'-bromo-7'-phenyl-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335770ノート

反応式

HRID 335770 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8](I)=[CH:9][CH:10]=3)[C@:5]3([CH2:20][O:19][C:18]([NH2:21])=[N:17]3)[C:4]=2[CH:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.O.C(OCC)(=O)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:9][CH:10]=3)[C@:5]3([CH2:20][O:19][C:18]([NH2:21])=[N:17]3)[C:4]=2[CH:3]=1

参加物

7

反応物 2

HCID 66827Phenylboronic AcidHCID 59272325(S)-2'-bromo-7'-iodo-5H-spiro[oxazole-4,9'-xanthen]-2-amine

生成物 1

HCID 67241122(R)-2'-bromo-7'-phenyl-5H-spiro[oxazole-4,9'-xanthen]-2-amine

試薬・触媒・溶媒 4

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A 100 ml RBF vial was charged with (S)-2′-bromo-7′-iodo-5H-spiro[oxazole-4,9′-xanthen]-2-amine (3.37 g, 7.37 mmol) in dioxane (30 mL), water (15 mL), phenylboronic acid (0.965 g, 7.91 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.106 g, 0.150 mmol), and potassium phosphate-tribasic (3.17 g, 14.93 mmol). The reaction was heated to 100° C. in an oil-bath for 8 hours. The reaction was diluted with ethyl acetate (100 mL), water (25 mL), and the ethyl acetate layer was separated and dried over anhydrous sodium sulfate. Concentration and purification by silica gel flash column chromatography (hexanes/ethyl acetate) provided (R)-2′-bromo-7′-phenyl-5H-spiro[oxazole-4,9′-xanthen]-2-amine

後処理

  1. customthe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationConcentration and purification by silica gel flash column chromatography (hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-94daeecd74564aa683e4a92d3401ed09
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

読み込み中…