7-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazine → 2-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]nicotinonitrile

HRID 586248Notes

Reaction equation

HRID 586248 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH:7]=1.[CH3:17][C:18]1([CH3:39])[CH2:23][O:22][B:21]([C:24]2[CH:25]=[CH:26][C:27]([F:38])=[C:28]([C:30]3[N:37]=[CH:36][CH:35]=[CH:34][C:31]=3[C:32]#[N:33])[CH:29]=2)[O:20][CH2:19]1.C(C1C(C2C=C(B(O)O)C=CC=2F)=NC=CC=1)#N.Br[C:59]1[N:63]2[N:64]=[CH:65][C:66]([C:68]([F:71])([F:70])[F:69])=[N:67][C:62]2=[N:61][CH:60]=1>>[CH3:17][C:18]1([CH3:39])[CH2:19][O:20][B:21]([C:24]2[CH:25]=[CH:26][C:27]([F:38])=[C:28]([C:30]3[N:37]=[CH:36][CH:35]=[CH:34][C:31]=3[C:32]#[N:33])[CH:29]=2)[O:22][CH2:23]1.[F:16][C:5]1[CH:4]=[CH:3][C:2]([C:59]2[N:63]3[N:64]=[CH:65][C:66]([C:68]([F:69])([F:70])[F:71])=[N:67][C:62]3=[N:61][CH:60]=2)=[CH:7][C:6]=1[C:8]1[N:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

6

Reactant 4

HCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 222852704-Fluoro-3-(3-cyanopyridin-2-yl)phenylboronic acidHCID 222852972-(5-Bromo-2-fluorophenyl)nicotinonitrileHCID 223294932-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]nicotinonitrile

Product 2

HCID 101780352-[2-Fluoro-5-(3-trifluoromethyl-imidazo[1,2-b][1,2,4]triazin-7-yl)phenyl]nicotinonitrileHCID 223294932-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]nicotinonitrileYield 40%

Procedure

2-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]nicotinonitrile was prepared from 2-(5-bromo-2-fluorophenyl)nicotinonitrile (1.36 g, 4.91 mmol) using the method described in Example 2 to give 467 mg (43%) of an approximately 1:1 mixture of 2-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]nicotinonitrile and 3-(3-cyanopyridin-2-yl)-4-fluorobenzeneboronic acid as a grey solid. This was coupled to 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine in 40% yield using the method described in Example 3 to give the title compound as a yellow solid: mp 209-211° C. (EtOAc); 1H NMR (360 MHz, CDCl3) δ 7.46 (1H, s), 7.54 (2H, m), 8.14 (1H, d, J 1.8 Hz), 8.37 (1H, m), 8.64 (1H, s), 8.82 (1H, s), 8.89 (1H, s). Anal. Found: C, 54.97; H, 2.30; N, 21.74%. Required for C18H8F4N6.0.5H2O: C, 54.97, H, 2.31; N, 21.37%.

Workup

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Sources & evidence

ORD record
ord-d0d3848421ce4e349093fccf5796f780
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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