1-(Azidomethyl)-3-(trifluoromethyl)benzene → HCID 59644546, compound

HRID 2251993Notes

Reaction equation

[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[N+:2]=[N-:3].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([C:24]1[C:25]([C:30]#[C:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23]>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([C:24]1[C:25]([C:30]2[N:3]=[N:2][N:1]([CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:13])([F:12])[F:14])[CH:6]=3)[C:31]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23]

Participants

Conditions

Temperature: 150 °C

Procedure

Add 1-azidomethyl-3-trifluoromethyl-benzene (152 mg, 0.75 mmol), (2-chloro-phenyl)-(2-pyridin-4-ylethynyl-pyridin-3-yl)-methanone (200 mg, 0.63 mmol), and toluene (2 mL) to a sealed tube. Flush with nitrogen, seal, and heat at 150° C. overnight. Concentrate to dryness and triturate with diethyl ether to afford the title compound (66 mg, 20%) as a pink solid: MS(IS) 520(M+1); TLC (5% MeOH/dichloromethane) Rf=0.48.

Workup

customFlush with nitrogen
customseal
concentrationConcentrate to dryness
customtriturate with diethyl ether

Sources & evidence

ORD record: ord-ecec17fe5d7a4f84828202b4e22daf85
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320994B2

Reaction notes

Loading…