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

HRID 1970364ノート

反応式

HRID 1970364 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-79df6c99ca324b1fbece64fa74fb372e
出典データセット
uspto-grants-2013_04
特許番号
US08426447B2

反応ノート

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