2-Bromo-5-chloropyridine → HCID 58580279, compound

HRID 1044418Notes

Reaction equation

HRID 1044418 reaction equation
[I-].[C:2]([O:10][CH2:11][Zn+])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:2]([O:10][CH2:11][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 8170982-Bromo-5-chloropyridineHCID 178525802HCID 178525802, compound

Product 1

HCID 58580279HCID 58580279, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Title compound was prepared according to the procedure described in: Hasnik, Z.; Silhar, P.; Hocek, M. Synlett 2008, 4, 543. A solution of (benzoyloxymethyl)zinc(II) iodide Part B (2.17 mL, 1.949 mmol) was added to a solution of 2-bromo-5-chloropyridine (125 mg, 0.650 mmol) and Pd(PPh3)4 (37.5 mg, 0.032 mmol) in THF (1.30 mL). The reaction mixture was stirred at RT for 5 h at which point it was quenched with 1M NaH2PO4 (30 mL) The solid formed was filtered and washed well with water. The filtrate was extracted with DCM (3×25 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated. The crude product was subjected to flash chromatography (silica gel/hexanes-EtOAc 100:0 to 50:50 gradient) to afford (5-chloropyridin-2-yl)methyl benzoate 16C (101 mg, 63% yield) as an off-white solid. LC-MS, [M+H]+=248. HPLC-Method 8; 3.30 min.

Workup

  1. customTitle compound was prepared
  2. customwas quenched with 1M NaH2PO4 (30 mL) The solid
  3. customformed
  4. filtrationwas filtered
  5. washwashed well with water
  6. extractionThe filtrate was extracted with DCM (3×25 mL)
  7. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-79160cb5d25f4638996dc6330fad5860
Source dataset
uspto-grants-2013_10
Patent number
US08563583B2

Reaction notes

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