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

HRID 1611934
Notes
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Reaction equation

HRID 1611934 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst
HCID 6228DimethylformamideSolvent

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

  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

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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes