Dimethylformamide → HCID 71547689, compound

HRID 1771155Notes

Reaction equation

HRID 1771155 reaction equation
C(=O)([O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][C:21](Cl)=[N:20]3)=[O:16])[C:9]=1[F:28])OC(C)(C)C.[CH3:30][N:31](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:28][C:9]1[C:8]([OH:7])=[CH:13][CH:12]=[C:11]([F:14])[C:10]=1[C:15]([C:17]1[CH:18]=[C:19]2[C:24]([N:23]=[CH:22][C:21]([C:30]#[N:31])=[N:20]2)=[CH:25][CH:26]=1)=[O:16]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 89484872HCID 89484872, compound

Product 1

HCID 71547689HCID 71547689, compoundYield 3%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4-difluorophenyl) carbonate (80 mg, 0.2 mmol, 1 eq.) in DMF (5 mL) were added Zn(CN)2 (20 mg, 0.12 mmol, 0.6 eq.), DPPF (4 mg, 0.0064 mmol, 0.032 eq.) and Pd2(dba)3 under N2 protection. The resulting mixture was stirred at 120° C. overnight, then cooled and concentrated. The residue was purified via prep-HPLC to afford 7-(2,6-difluoro-3-hydroxybenzoyl)quinoxaline-2-carbonitrile as yellow oil (1.8 mg, 3%). LRMS (M−H+) m/z calculated 310.1, found 309.9. 1H NMR (CDCl3, 400 MHz) δ 9.18 (s, 1 H), 8.52-8.56 (m, 2H), 8.33-8.35 (d, 1 H), 7.18-7.24 (m, 1 H), 6.96-7.01 (m, 1 H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was purified via prep-HPLC

Sources & evidence

ORD record
ord-8505cc370557439ea2faee4ef9258cfe
Source dataset
uspto-grants-2016_02
Patent number
US09249111B2

Reaction notes

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