Diethyl Ether → 3-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridine

HRID 269582ノート

反応式

HRID 269582 の反応式
[CH2:1]([O:8][C:9]1[C:14](Br)=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:14]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][CH:11]=[C:12]([Cl:16])[CH:13]=1

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 2773294(2-Bromophenyl)boronic acidHCID 220583822-(Benzyloxy)-3-bromo-5-chloropyridine

生成物 1

HCID 587309973-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridine収率 42.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 21863594Toluene ethanol溶媒

反応条件

温度
70 °C

実験手順

2-(Benzyloxy)-3-bromo-5-chloropyridine (150 mg, 0.5 mmol) and 2-bromophenylboronic acid (100 mg, 0.5 mmol) were dissolved in toluene/ethanol (1:1, 5 ml) under nitrogen. Potassium carbonate (550 mg, 4 mmol) was added, followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The resulting mixture was heated at 70° C. in a Smithcreator® microwave for 10 minutes. After cooling, diethyl ether(10 ml) and water (10 ml) were added, The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane) to give the title compound as a clear oil (80 mg).

後処理

  1. temperatureAfter cooling
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane)

出典と根拠

ORDレコード
ord-0619a99b59864bf8a00077c1d42ed192
出典データセット
uspto-grants-2008_11
特許番号
US07446222B2

反応ノート

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