2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → HCID 10178521, compound

HRID 586257Notes

Reaction equation

HRID 586257 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]([OH:38])([CH3:37])[CH3:36])=[N:34][C:29]2=[N:28][CH:27]=1>>[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]([OH: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

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 11336372HCID 11336372, compound

Product 1

HCID 10178521HCID 10178521, compoundYield 54%

Procedure

5′-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-4,2′-difluorobiphenyl-2-carbonitrile (see Example 4) was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol in 54% yield using a similar procedure to that described in Example 3, step f, to give a yellow solid: mp 215° C.; 1H NMR (360 MHz, CDCl3) δ 1.71 (6H, s), 3.27 (1H, br s), 7.35-7.59 (4H, m), 8.09-8.15 (2H, m), 8.26 (1H, s), 8.78 (1H, s); MS (ES+) m/z 392 [M+H]+. Anal. Found: C, 64.38; H, 3.88; N, 17.66%. Required for C21H15F2N5O: C, 64.45; H, 3.86; N, 17.89%.

Workup

  1. customto give a yellow solid

Sources & evidence

ORD record
ord-79c5d01d385a4d82ae5c6094a2dc417c
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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