Benzyl Alcohol → 8-Benzyloxy-7-bromo-2-methoxy-[1,5]naphthyridine

HRID 1422826Notes

Reaction equation

HRID 1422826 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Br:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[OH:24])=[N:21][C:20]([O:25][CH3:26])=[CH:19][CH:18]=2.[CH2:27](O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[CH2:27]([O:24][C:23]1[C:14]([Br:13])=[CH:15][N:16]=[C:17]2[C:22]=1[N:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18]2)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178487833HCID 178487833, compound

Product 1

HCID 667463738-Benzyloxy-7-bromo-2-methoxy-[1,5]naphthyridineYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl azodicarboxylate (1.37 g, 7.84 mmol, 2.0 eq) is added at room temperature to a stirred solution of 3-bromo-6-methoxy-[1,5]naphthyridin-4-ol (1.0 g, 3.92 mmol, 1.0 eq), benzyl alcohol (640 mg, 5.88 mmol, 1.5 eq) and triphenylphosphine (2.05 g, 7.84 mmol, 2.0 eq) in tetrahydrofuran (25 mL). After 15 hours stirring at room temperature, tetrahydrofuran is evaporated and the resulting crude product is purified by column chromatography (silica gel, eluent: petroleum ether: ethyl acetate, 10:1, v/v) to afford 8-benzyloxy-7-bromo-2-methoxy-[1,5]naphthyridine as a white solid (1.0 g, 74% yield).

Workup

  1. customtetrahydrofuran is evaporated
  2. customthe resulting crude product is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-85d1718f9bb9469a8878d6575f7f576e
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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