(4-Methoxyphenyl)boronic acid → HCID 11524517, compound

HRID 1991463Notes

Reaction equation

HRID 1991463 reaction equation
Br[C:2]1[S:10][C:9]2[N:8]=[C:7]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:6]3=[C:5]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:4]=2[C:3]=1[C:21]#[N:22].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].COCCOC.O>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[S:10][C:9]3[N:8]=[C:7]4[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:6]4=[C:5]([C:16]4[S:17][CH:18]=[CH:19][CH:20]=4)[C:4]=3[C:3]=2[C:21]#[N:22])=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 516892Sodium BicarbonateHCID 11560163HCID 11560163, compound

Product 1

HCID 11524517HCID 11524517, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a Schlenk tube was added 2-bromo-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]indene-3-carbonitrile (45 mg, 0.116 mmol), p-methoxyphenyl boronic acid (21 mg, 0.138 mmol), NaHCO3 (29 mg, 0.348 mmol), Bu4NBr (8 mg, 0.023 mmol) and 1 mL of DME/H2O (4/1). After evacuating and back-filling with nitrogen twice, a catalytic amount of Pd(PPh3)4 was added. The sealed mixture was heated to 80° C. overnight. After pouring into water, the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous MgSO4 and concentrated. The residue was purified by flash chromatography to provide 30 mg of the title compound, 2-(4-methoxyphenyl)-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]indene-3-carbonitrile.

Workup

  1. customAfter evacuating and back-filling with nitrogen twice
  2. additiona catalytic amount of Pd(PPh3)4 was added
  3. additionAfter pouring into water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5c3738f9c5794924af35559e54bbe8e0
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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