2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → PharmaGSID_47330

HRID 586266Notes

Reaction equation

HRID 586266 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:24]#[N:25])[C:7]=1[C:8]1[CH:13]=[C:12](B2OC(C)(C)C(C)(C)O2)[CH:11]=[CH:10][C:9]=1[F:23].Br[C:27]1[N:31]2[N:32]=[CH:33][C:34]([C:36]([OH:39])([CH3:38])[CH3:37])=[N:35][C:30]2=[N:29][CH:28]=1>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:24]#[N:25])[C:7]=1[C:8]1[CH:13]=[C:12]([C:27]2[N:31]3[N:32]=[CH:33][C:34]([C:36]([OH:39])([CH3:37])[CH3:38])=[N:35][C:30]3=[N:29][CH:28]=2)[CH:11]=[CH:10][C:9]=1[F:23]

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 114732892′,6-Difluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

Product 1

HCID 9865233PharmaGSID_47330

Procedure

6,2′-Difluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol in 32% yield using a similar procedure to that described in Example 3, step f, to give a yellow solid: mp 206° C.; 1H NMR (360 MHz, CDCl3) δ 1.71 (6H, s), 3.28 (1H, br s), 7.37-7.66 (4H, m), 8.15 (2H, m), 8.26 (1H, s), 8.78 (1H, s); MS (ES+) m/z 392 [M+H]+. Anal. Found: C, 64.66; H, 3.93, N, 17.71%. Required for C21H15F2N5O: C, 64.45; H, 3.86; N, 17.89%.

Workup

  1. customto give a yellow solid

Sources & evidence

ORD record
ord-db74c4cbe74a41fb982a96936b5166d5
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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