Sodium Carbonate → 7-Benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridine

HRID 633800Notes

Reaction equation

HRID 633800 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[CH2:23]O)=[N:20][C:19]([O:25][CH3:26])=[CH:18][CH:17]=2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:5]([O:12][C:13]1[C:22]([CH2:23][Br:2])=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([O:25][CH3:26])=[N:20]2)=[N:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 67255949(3-Benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-methanol

Product 1

HCID 867306967-Benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridineYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus tribromide (32 μL, 0.34 mmol, 2.0 eq) is added at room temperature to a stirred solution of (3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-yl)-methanol (50 mg, 0.17 mmol, 1.0 eq) in dichloromethane (5 mL). After 1 hour stirring at room temperature, pH of the reaction mixture is adjusted to 7 by the addition of a sodium carbonate aqueous solution. The resulting solution is extracted with dichloromethane (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 7-benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridine as a white solid (62 mg, 99% yield).

Workup

  1. extractionThe resulting solution is extracted with dichloromethane (3×10 mL) and water (10 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb603d11853041ddb457d807d081d346
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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