HCID 11336372, compound → HCID 10222165, compound

HRID 586234Notes

Reaction equation

HRID 586234 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:23])=[C:12]([C:14]3[C:15]([C:21]#[N:22])=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[CH:13]=2)OC1.Br[C:26]1[N:30]2[N:31]=[CH:32][C:33]([C:35]([F:38])([CH3:37])[CH3:36])=[N:34][C:29]2=[N:28][CH:27]=1.CCOC(C)=O.CCCC(C)C>>[F:20][C:17]1[CH:16]=[C:15]([C:21]#[N:22])[C:14]([C:12]2[CH:13]=[C:8]([C:26]3[N:30]4[N:31]=[CH:32][C:33]([C:35]([F:38])([CH3:36])[CH3:37])=[N:34][C:29]4=[N:28][CH:27]=3)[CH:9]=[CH:10][C:11]=2[F:23])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 11336372HCID 11336372, compoundHCID 11459593HCID 11459593, compoundHCID 21882781Isohexane ethyl acetate

Product 1

HCID 10222165HCID 10222165, compound

Procedure

5′-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-4,2′-difluorobiphenyl-2-carbonitrile was coupled to 7-bromo-3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine in 77% yield using a similar procedure to that described in Example 3, step f, to give a yellow solid: mp 156-159° C. (EtOAc-isohexane); 1H NMR (400 MHz, CDCl3) δ 1.84 (6H, d, J 22.0 Hz), 7.36-7.46 (2H, m), 7.54 (1H, dd, J 7.8, 2.7 Hz), 7.57-7.60 (1H, m), 8.10-8.16 (2H, m), 8.30 (1H, s), 8.79 (1H, d, J 1.2 Hz); MS (ES+) m/z 394 [M+H]+. Anal. Found: C, 64.07; H, 3.66; N, 17.60%. Required for C21H14F3N5: C, 64.12; H, 3.59; N, 17.80%.

Workup

  1. customto give a yellow solid

Sources & evidence

ORD record
ord-aa439645d5854a1b96d157e0329b2a10
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

Loading…