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

HRID 1422826노트

반응식

HRID 1422826 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-85d1718f9bb9469a8878d6575f7f576e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927542B2

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