4-Cyanophenylboronic acid → HCID 58424788, compound

HRID 2096399Notes

Reaction equation

HRID 2096399 reaction equation
[NH2:1][C:2]1[N:3]([CH2:24][CH3:25])[C:4](=[O:23])[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]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.[C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#[N:27]>C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]([CH2:24][CH3:25])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:30]4[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=4)[C:26]#[N:27])[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1

Participants

6

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 58423775HCID 58423775, compound

Product 1

HCID 58424788HCID 58424788, compoundYield 4.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Pd(PPh3)4 (40 mg, 0.10 mmol) in a 10 mL flask under Ar was treated sequentially with 2′-amino-6-bromo-1′-ethyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (42 mg, 0.10 mmol) in toluene (5 mL), Na2CO3 (2 N, 2 mL), and 4-cyanophenylboronic acid (31 mg, 0.21 mmol). The mixture refluxed under Ar overnight. The reaction mixture was concentrated in vacuo to give a residue, which was purified by preparative TLC followed by preparative HPLC to give pure 3-(2′-amino-1′-ethyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (1.76 mg, 3%). 1H-NMR (MeOD): 1.31 (m, 3H), 2.55 (m, 2H), 3.84 (m, 2H), 5.26 (m, 1H), 5.86 (m, 1H), 7.14 (m, 1H), 7.47 (m, 6H), 7.59 (m, 1H), 7.28 (m, 2H), 7.90 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-bcf1a89348ee4060a634ea6053ec77cc
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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