Benzyl Bromide → HCID 57980514, compound

HRID 41507Notes

Reaction equation

HRID 41507 reaction equation
C(Br)C1C=CC=CC=1.[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:14][C:15]=1[CH3:16].C(N(CC)CC)C.[H][H]>C(O)(C)C.[C].[Pd]>[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([C:17]2[CH2:18][NH:19][CH2:20][CH2:21][CH:22]=2)=[N:14][C:15]=1[CH3:16]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 23555885HCID 23555885, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57980514HCID 57980514, compoundYield 19.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl bromide in an amount of 1.06 g was added to a solution of 1 g of 5,6-dimethyl-2,3′-bipyridine in 15 mL of isopropyl alcohol, and stirred for 5 hours at 50° C. to finish the reaction. To the reaction solution, 0.18 g of 10% palladium carbon and 0.59 g of triethylamine were added. This admixture was put in an autoclave, the autoclave's atmosphere was replaced twice with nitrogen gas under a nitrogen pressure of 196 kPa, and then hydrogen gas was blown into the autoclave over 3 hours at 80° C. under a hydrogen pressure of 196 kPa until the absorption of hydrogen gas in a volume of 400 mL was completed. After the replacement with nitrogen, the catalyst was filtered out and the resulting filtrate was concentrated under a reduced pressure of 1.33 kPa until the quantity thereof was reduced to 1.70 g. Further thereto, 50 mL of water and 10 g of a 25% aqueous solution of sodium hydroxide were added. The resulting solution was extracted with three 200 mL portions of ethyl acetate, and the organic layer was concentrated. The thus obtained solid was adsorbed to NH2-modified silica gel (produced by Biotage Japan, Ltd.), and eluted with ethyl acetate. The fraction obtained was concentrated, and the crystals thus deposited were dried to give 0.20 g of the entitled compound as light yellow crystals. Yield rate: 20%, EI-MS: (m/z) 188 (M+), melting point: 102-104° C.

Workup

  1. customthe reaction
  2. custompressure of 196 kPa until the absorption of hydrogen gas in a volume of 400 mL
  3. filtrationAfter the replacement with nitrogen, the catalyst was filtered out
  4. concentrationthe resulting filtrate was concentrated under a reduced pressure of 1.33 kPa until the quantity
  5. additionFurther thereto, 50 mL of water and 10 g of a 25% aqueous solution of sodium hydroxide were added
  6. extractionThe resulting solution was extracted with three 200 mL portions of ethyl acetate
  7. concentrationthe organic layer was concentrated
  8. washeluted with ethyl acetate
  9. customThe fraction obtained
  10. concentrationwas concentrated
  11. customthe crystals thus deposited were dried

Sources & evidence

ORD record
ord-c09cee14e46348daa764d190d0a8175e
Source dataset
uspto-grants-2013_09
Patent number
US08530662B2

Reaction notes

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