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

HRID 269582노트

반응식

HRID 269582 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 21863594Toluene ethanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0619a99b59864bf8a00077c1d42ed192
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

반응 노트

불러오는 중…