Sodium Carbonate → 4-(4-Formylpyridin-3-yl)-2-methoxybenzonitrile

HRID 1897619Notes

Reaction equation

HRID 1897619 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Br[C:21]1[CH:28]=[N:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH:23]([C:22]1[CH:21]=[CH:28][N:27]=[CH:26][C:25]=1[C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1)=[O:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 595783882-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 866748424-(4-Formylpyridin-3-yl)-2-methoxybenzonitrileYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (259 mg, 1 mmol), 3-bromoisonicotinaldehyde (186 mg, 1.000 mmol), a solution of sodium carbonate (2M in water, 1.000 ml, 2.000 mmol), bis(triphenylphosphine)palladium(11) chloride (17.55 mg, 0.025 mmol) in DMF (6 mL, dry) was heated to 120° C. for 3 hrs. After concentration, the residue was dissolved into CH2Cl2-MeOH and mixed with silica gel and concentrated. After flash column (MeOH—CH2Cl2, v/v, 0.5%-1%) yielded colorless solid (170 mg). 1H NMR (400.3 MHz, CDCl3): δ 3.99 (s, 3H), 6.98 (d, J=1.32 Hz, 1H), 7.05 (dd, J=1.48, 7.8 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.81 (d, J=5 Hz, 1H), 8.81 (s, 1H), 8.90 (d, J=5 Hz, 1H), 10.04 (s, 1H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved into CH2Cl2-MeOH
  3. additionmixed with silica gel
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4ed7dfcf63cd46e59f7718c3534b2580
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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