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

HRID 1422826ノート

反応式

HRID 1422826 の反応式
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

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178487833HCID 178487833、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-85d1718f9bb9469a8878d6575f7f576e
出典データセット
uspto-grants-2015_01
特許番号
US08927542B2

反応ノート

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