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

HRID 1970364노트

반응식

HRID 1970364 반응식
[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

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-79df6c99ca324b1fbece64fa74fb372e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426447B2

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