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

HRID 1611934Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-a2c07edda6fd4cd68efd06c08424e761
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992083B2

Reaction notes

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