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3-Cyanophenylboronic acid → HCID 67384974, compound

HRID 1408774
Notes
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Reaction equation

HRID 1408774 reaction equation
[NH2:1][C:2]1[N:3]([CH2:24][C:25]([F:28])([F:27])[F:26])[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:29]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)#[N:30]>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]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:35]4[CH:36]=[C:31]([CH:32]=[CH:33][CH:34]=4)[C:29]#[N:30])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 584246322'-amino-6-bromo-2-phenyl-1'-(2,2,2-trifluoroethyl)spiro[chroman-4,4'-imidazol]-5'(1'H)-one

Product 1

HCID 67384974HCID 67384974, compoundYield 17.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst
HCID 10796
Cesium carbonate
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

Pd(PPh3)2Cl2 (10 mg) in a 10 mL of tube under Ar2 was treated sequentially with 2′-amino-6-bromo-2-phenyl-1′-(2,2,2-trifluoroethyl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.044 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 M, 0.3 mL) and 3-cyanophenylboronic acid (13 mg, 0.088 mmol). The mixture was heated at 120 under microwave reactor for 0.5 h. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give pure 3-(2′-amino-5′-oxo-2-phenyl-1′-(2,2,2-trifluoroethyl)-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (3.7 mg, 12%). 1H-NMR (MeOD): 2.27 (m, 1H), 2.35 (m, 1H), 3.87 (m, 2H), 5.83 (m, 1H), 7.01 (d, 1H), 7.26 (m, 1H), 7.32 (m, 5H), 7.59 (m, 3H), 7.76 (m, 1H), 7.81 (m, 1H).

Workup

  1. temperatureThe mixture was heated at 120 under microwave reactor for 0.5 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-dac50d0430a5484c93d8ac89dde68970
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921359B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes