Triphenylphosphine → (4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanamine

HRID 1172936Notes

Reaction equation

[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([Cl:26])[CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Cl:26][C:18]1[CH:17]=[C:16]([C:13]2[N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=3)[O:15][N:14]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH:23]([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-(4-(azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazole (0.066 g, 0.178 mmol) in THF (3.40 ml) and water (0.170 ml) was added polymer-supported triphenylphosphine (0.237 g, 0.711 mmol). After about 2 h the reaction mixture was heated to about 60° C. After about 1 h the reaction mixture was cooled to room temperature, filtered, concentrated in vacuo and purified by chromatography on silica gel (eluting with MeOH:DCM) to provide (4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanamine (40 mg, 64%) as a colorless solid.

Workup

temperatureAfter about 1 h the reaction mixture was cooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by chromatography on silica gel (eluting with MeOH:DCM)

Sources & evidence

ORD record: ord-01a683ec8b7d408ba5608bb835e7ba54
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834039B2

Reaction notes

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