Bromotrimethylsilane → 4-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one

HRID 1783671ノート

反応式

HRID 1783671 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12]O)=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1.C[Si]([Br:22])(C)C.[Li+].[Br-]>CC#N>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][Br:22])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1

参加物

5

反応物 3

HCID 76113BromotrimethylsilaneHCID 82050Lithium BromideHCID 21106569HCID 21106569、化合物

生成物 1

HCID 211065684-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one収率 44.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of 4-bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.74 g, 2.5 mmol) in MeCN (5 ml) was added dropwise to a stirred suspension of trimethylsilyl bromide (TMSBr) (0.9 g, 6.3 mmol) and LiBr (0.41 g, 5 mmol) in MeCN (15 ml). The reaction mixture was heated to 80° C. for 24 hours, after which time the reaction mixture was cooled to RT and the solvent removed under vacuum. The resulting residue was purified by flash column chromatography (elution: 85% heptane, 15% EtOAc) to give the title compound (0.4 g, 44% yield) as a white solid. 1H-NMR: (250 MHz, D6- DMSO), 8.37 (1H, s), 8.03 (1H, d), 7.94 (1 H, d), 5.26-5.09 (1H, m), 4.93 (2H, s), 1.35 (6H, d).

後処理

  1. temperatureafter which time the reaction mixture was cooled to RT
  2. customthe solvent removed under vacuum
  3. customThe resulting residue was purified by flash column chromatography (elution: 85% heptane, 15% EtOAc)

出典と根拠

ORDレコード
ord-02daeccc312a4d1cbe22a79517ab5588
出典データセット
uspto-grants-2009_03
特許番号
US07501410B2

反応ノート

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