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Triphenylarsine → 4-Methoxy-7-phenyl-benzooxazol-2-ylamine

HRID 1611934
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인쇄 미리보기

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HRID 1611934 반응식
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[C:18]1([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Cu]I>[CH3:16][O:15][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[O:6][C:7]=2[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1
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참가 물질

7

반응물 3

HCID 11773TriphenylarsineHCID 607632TributylphenyltinHCID 23593642(7-Iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester

생성물 1

HCID 222522314-Methoxy-7-phenyl-benzooxazol-2-ylamine수율 35.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 9832798
Tris(dibenzylideneacetone) dipalladium
촉매
HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a stirred solution of 820 mg (2.36 mmol) (7-iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 20 ml N,N-dimethylformamide were added 1.17 ml (3.58 mmol) phenyltri-n-butylstannane, 162 mg (0.18 mmol) tris(dibenzylideneacetone) dipalladium(0), 65 mg (0.21 mmol) triphenylarsine and 208 mg (1.09 mmol) copper(I) iodide. The mixture was heated at 80° C. for 16 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (1/99 methanol/dichloromethane) followed by trituration in ether afforded 200 mg 4-methoxy-7-phenyl-benzooxazol-2-yl-amine as a white solid. ES-MS m/e (%): 241 (M+H+, 100).

후처리

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a2c07edda6fd4cd68efd06c08424e761
출처 데이터셋
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06992083B2

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