4-Cyanophenylboronic acid → HCID 58424630, compound

HRID 2096420Notes

Reaction equation

HRID 2096420 reaction equation
[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:7]2)[N:6]=1.[C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)#[N:28]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:31]4[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=4)[C:27]#[N:28])[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:7]2)[N:6]=1

Participants

6

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 58423822HCID 58423822, compound

Product 1

HCID 58424630HCID 58424630, compoundYield 20.7%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 10796Cesium carbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

Pd(PPh3)2Cl2 (20 mg) in a 10 mL flask under Ar was treated sequentially with 2′-amino-6-bromo-2-(3-methoxyphenyl)-1′-methylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (46 mg, 0.11 mmol) in 1,4-dioxane (5 mL), Cs2CO3 (2 N, 0.5 mL) and 4-cyanophenylboronic acid (32.6 mg, 0.22 mmol). The mixture was refluxed under Ar for 2 h. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC followed by preparative HPLC to give pure 3-(2′-amino-2-(3-methoxyphenyl)-1′-methyl-5′-oxo-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (10 mg, 20%). 1H-NMR (CDCl3): 2.26 (m, 1H), 2.48 (m, 1H), 3.72 (s, 3H), 5.62 (m, 1H), 6.79 (m, 3H), 6.94 (d, 1H), 7.12 (d, 1H), 7.20 (s, 1H), 7.29 (m, 1H), 7.36 (m, 1H), 7.41 (t, 1H), 7.61 (d, 2H).

Workup

  1. temperatureThe mixture was refluxed under Ar for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give the residue, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-31306cf99ce94473aa193c5f36167fab
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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