Triphenylphosphine → 5-[(2-Chloro-4-pyrimidinyl)ethynyl]-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 536165Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[C:15]([CH:18]=1)[C:16]#[N:17])#[CH:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu]I.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:10]#[C:9][C:11]2[CH:12]=[CH:13][C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of copper(I) iodide (117 mg, 0.613 mmol), dichloropalladium-triphenylphosphane (1:2) (215 mg, 0.306 mmol), 2,4-dichloropyrimidine (913 mg, 6.13 mmol), and 5-ethynyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (880 mg, 3.06 mmol) in a mixed solvents of TEA (18 mL, 129 mmol) and tetrahydrofuran (12 mL), was added triphenylphosphine (161 mg, 0.613 mmol) under Argon. The reaction mixture was stirred for 12 h at 60° C., filtered, washed with EA, concentrated. Purification via ISCO system (EtOAc=1:20 to 1:5) afforded the title compound as a brown solid. LC-MS (ESI): m/z 400 [M+H]+; 3.86 min (ret time).

Workup

filtrationfiltered
washwashed with EA
concentrationconcentrated
customPurification via ISCO system (EtOAc=1:20 to 1:5)

Sources & evidence

ORD record: ord-230ad4f9db334578a1e8691785ff5ace
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859573B2

Reaction notes

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