Sodium Carbonate → HCID 86674839, compound

HRID 1897592Notes

Reaction equation

HRID 1897592 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[C:20]1[CH:27]=[N:26][CH:25]=[CH:24][C:21]=1[CH:22]=[O:23].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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>[Cl:1][C:2]1[CH:9]=[C:8]([C:24]2[CH:25]=[N:26][CH:27]=[CH:20][C:21]=2[CH:22]=[O:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 579261132-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 86674839HCID 86674839, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (0.264 g, 1 mmol), 3-bromoisonicotinaldehyde (0.186 g, 1.000 mmol), sodium carbonate (1.000 ml, 2.000 mmol), bis(triphenylphosphine)palladium(II) chloride (0.018 g, 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 2-chloro-4-(4-formylpyridin-3-yl)benzonitrile (20a) as colorless solid (170 mg) 1H NMR (400.3 MHz, CDCl3): δ 7.63 (d, J=8.0 Hz, 1H), 7.79 (s, 1H), 7.83 (d, J=8.0 Hz, 1H), 8.35 (s, 1H), 9.07 (s, 1H), 9.15 (s, 1H), 10.22 (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-5a79e39b465a448a98b741ff82d6cf36
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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