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Potassium Carbonate → HCID 86698652, compound

HRID 1054649
Notes
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Reaction equation

HRID 1054649 reaction equation
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CCO.C1(C)C=CC=CC=1.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.Cl[Pd]Cl.[Fe+2]>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([CH3:10])[CH:9]=2)=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 57736551HCID 57736551, compound

Product 1

HCID 86698652HCID 86698652, compoundYield 24.9%

Reagents, catalysts & solvents 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-4-methyl-5-nitro-benzonitrile (522.0 mg, 2.17 mmol), 4-methoxyphenyl boronic acid (329.0 mg, 2.17 mmol) and 2 N aqueous potassium carbonate (6.56 mL, 13.1 mmol) in EtOH (6 mL) and toluene (3 mL) was degassed with N2 for 5 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (180.0 mg, 0.22 mmol), and degassed with N2 for an additional 5 minutes. The reaction mixture was sealed and heated to 80° C. for 3 hours. The reaction was cooled to room temperature and the layers were separated. The organic layer was filtered and the solids were air dried to give the title compound (145 mg). The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (25-75% EtOAc/heptane) to give the title compound (337 mg). The two lots of the title compound were combined (482 mg, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.59 (s, 1 H), 7.78 (s, 1 H), 7.63 (d, J=8.78 Hz, 2 H), 7.14 (d, J=8.59 Hz, 2 H), 3.85 (s, 3 H), 2.64 (s, 3 H).

Workup

  1. customwas degassed with N2 for 5 minutes
  2. customdegassed with N2 for an additional 5 minutes
  3. customThe reaction mixture was sealed
  4. temperatureThe reaction was cooled to room temperature
  5. customthe layers were separated
  6. filtrationThe organic layer was filtered
  7. customdried

Sources & evidence

ORD record
ord-f3bcd34c92f04a71845670c792170956
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394285B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes