Sodium Carbonate → HCID 52937043, compound

HRID 1175150Notes

Reaction equation

HRID 1175150 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.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>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 52937043HCID 52937043, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

3,5-Dibromopyridine (ABCR Product List AB115322) (250 mg; 2.1 mmol), 2-fluorophenylboronic acid (Sigma-Aldrich, order number 445223)(147 mg; (2.1 mmol), Pd(PPh3)2Cl2 (148 mg; 0.4 mmol) are combined in DMF (8 ml) and 2N Na2CO3 (1.3 ml) and heated to 160° C. in an oil bath for 20 minutes. The reaction mixture is evaporated to dryness, taken up in TBME/CH2Cl2 (30 ml/10 ml), diluted with hexanes (50 ml), filtered and evaporated to dryness. The solid white residue is dissolved in TBME (10 ml), diluted with hexanes, filtered, and purified via chromatography (SiO2, TBME/hexanes 5:95) to yield the title compound as white crystals (125 mg; 47%). MS (m/z) ES+: 252, 254 (MH+). Retention time: 2.79 minutes (LC-MS method 3).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. additiondiluted with hexanes (50 ml)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dissolutionThe solid white residue is dissolved in TBME (10 ml)
  6. additiondiluted with hexanes
  7. filtrationfiltered
  8. custompurified via chromatography (SiO2, TBME/hexanes 5:95)

Sources & evidence

ORD record
ord-d8391c433f9f4e7f8d15aea8d9519db2
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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