Phosphorus oxybromide → 5-Bromo-1,2,3,4-tetrahydro-2-(phenylmethyl)-2,6-naphthyridine

HRID 1890754Notes

Reaction equation

HRID 1890754 reaction equation
P(Br)(Br)([Br:3])=O.[CH2:6]([N:13]1[CH2:22][CH2:21][C:20]2[C:19](=O)[NH:18][CH:17]=[CH:16][C:15]=2[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>C1(OC)C=CC=CC=1.C(#N)C.ClCCl>[CH2:6]([N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[N:18][C:19]=2[Br:3])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 223351906-benzyl-5,6,7,8-tetrahydro-2,6-naphthyridin-1(2H)-one

Product 1

HCID 223354025-Bromo-1,2,3,4-tetrahydro-2-(phenylmethyl)-2,6-naphthyridine

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Phosphorous oxybromide (7.5 g, 26 mmol) is added portion wise to a suspension of 6-benzyl-5,6,7,8-tetrahydro-2,6-naphthyridin-1(2H)-one (1.6 g, 6.7 mmol) in anisole (20 mL) and acetonitrile (10 mL). The reaction mixture is stirred under reflux for 4 hours. The cooled mixture is poured onto ice and diluted with dichloromethane. The mixture is slowly neutralized using saturated sodium bicarbonate solution. The aqueous phase is extracted with dichloromethane three times. The organic phase are combined and washed with brine, dried over Na2SO4 and taken to dryness by rotary evaporation. The crude product as purified by column chromatography on silica gel to afford 2-benzyl-5-bromo-1,2,3,4-tetrahydro-2,6-naphthyridine as a white solid. MS m/z 303.1 (M+1).

Workup

  1. temperatureunder reflux for 4 hours
  2. additionThe cooled mixture is poured onto ice
  3. extractionThe aqueous phase is extracted with dichloromethane three times
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customtaken to dryness by rotary evaporation
  7. customThe crude product as purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1750751994044f53bc7af08940a1b7be
Source dataset
uspto-grants-2013_08
Patent number
US08507491B2

Reaction notes

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