Nitrogen → 8-Bromo-2-vinylquinoline

HRID 1041955

반응식

HRID 1041955 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Br:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:13](OB([O-])[O-])=[CH2:14].C(N(CC)CC)C.N#N>C1COCC1.CC(O)C.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH:13]=[CH2:14])[CH:11]=[CH:10]2

참가 물질

8

반응물 4

HCID 947NitrogenHCID 8471TriethylamineHCID 459259512,8-DibromoquinolineHCID 86654342Vinylborate

생성물 1

HCID 672347808-Bromo-2-vinylquinoline

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 22597222Tetrahydrofuran 2-propanol용매HCID 22728543Water ethylacetate용매

반응 조건

온도
55 °C

실험 절차

To 2,8-dibromoquinoline (1.836 g, 6.398 mmol) in THF/IPA (20 mL/10 mL) was added vinylborate (0.9428 g, 7.038 mmol) and triethylamine (0.7769 g, 7.678 mmol). The reaction mixture was purged with N2, and PdCl2(dppf) dichloromethane adduct (0.3685 g, 0.4479 mmol) was added. The reaction was stirred at 55° C. for 12 hours, then cooled to ambient temperature. The reaction mixture was diluted with EtOAc/H2O, and the organic layer was separated and concentrated to provide the crude product.

후처리

  1. additionwas added
  2. temperaturecooled to ambient temperature
  3. customthe organic layer was separated
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c3839b95bf424f1f8b545afef0bba66f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557809B2

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