N-Methylaniline → {4-[4-(2-Benzyloxy-ethyl)-5-methyl-oxazol-2-yl]-phenyl}-methyl-phenyl-amine

HRID 1181024Notes

Reaction equation

HRID 1181024 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[CH3:45][NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([N:46]([CH3:45])[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7515N-MethylanilineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 179843944-[2-(Benzyloxy)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazoleHCID 23676156Sodium t-butoxide

Product 1

HCID 17984359{4-[4-(2-Benzyloxy-ethyl)-5-methyl-oxazol-2-yl]-phenyl}-methyl-phenyl-amineYield 91%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 4-(2-benzyloxy-ethyl)-2-(4-bromo-phenyl)-5-methyl-oxazole (200 mg, 0.538 mmol) in toluene (5.0 mL) in a seal tube under nitrogen gas flow was treated with Pd(OAc)2 (50 mg), 2-(di-t-butylphosphino)biphenyl (20 mg), N-methyl aniline (115 mg, 1.08 mmol), and sodium t-butoxide (104 mg, 1.08 mmol). The tube was sealed and heated at 105° C. for 14 h. The mixture was cooled and purified directly by silica gel column chromatography (30-50% EtOAc/hexanes) to yield the title compound (195 mg, 91%). MS (ESI) m/z 399.3 (M+H)+.

Workup

  1. customThe tube was sealed
  2. temperatureThe mixture was cooled
  3. custompurified directly by silica gel column chromatography (30-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ba8e937a8e5b433792be0192b5991f82
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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