Nitrogen → 8-Bromo-2-vinylquinoline

HRID 339668

Reaction equation

HRID 339668 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 672347808-Bromo-2-vinylquinoline

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 22597222Tetrahydrofuran 2-propanolSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
55 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-038c80a14fc94d0f85367248780f1fd4
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Linked notes

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