4-(Cyanomethyl)benzeneboronic acid → {3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-biphenyl-4-yl}-acetonitrile

HRID 2096743Notes

Reaction equation

HRID 2096743 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:27])[C:9]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]=3[CH:26]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:28])[CH:3]=1.[C:29]([CH2:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)#[N:30]>>[Cl:28][C:4]1[CH:3]=[C:2]([C:35]2[CH:36]=[CH:37][C:32]([CH2:31][C:29]#[N:30])=[CH:33][CH:34]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:27])[C:9]([OH:14])([C:15]1[CH:16]=[CH:17][C:18]2[O:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]=2[CH:26]=1)[C:10]([F:13])([F:12])[F:11]

Participants

3

Reactant 2

HCID 27733424-(Cyanomethyl)benzeneboronic acidHCID 666971866-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 66697326{3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-biphenyl-4-yl}-acetonitrile

Procedure

In analogy to Example 17, step 2, 6-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (Example 22, step 3) was reacted with 4-cyanomethylphenylboronic acid to give the title compound as a colorless solid. MS (m/e)=515.4 [M+H+].

Sources & evidence

ORD record
ord-f58c664eb53b4f0ba3fe2d5fa798556f
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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