Quinoline → HCID 9927236, compound

HRID 860980Notes

Reaction equation

HRID 860980 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Li][CH:12]([CH2:14]C)[CH3:13].Br[C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>CCOCC.[NH4+].[Cl-].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.CCO>[C:19]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=[C:17]([C:9]2[CH:8]=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)[CH:18]=1

Participants

9

Reactant 4

HCID 7047QuinolineHCID 10340Sodium CarbonateHCID 164493-BromobiphenylHCID 178418400CID 53628100

Product 1

HCID 9927236HCID 9927236, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of Quinoline 1 (1.0 eq.) in Et2O (0.1M) at −78° C. was added dropwise sec-BuLi (1.0 eq.). The mixture was stirred for 15 min then tri-isopropyl boronate (1.1 eq.) was added. The final mixture was warm to rt and concentrated. To the residue was added 3-bromo-1,1′ biphenyl (1.5 eq.), Na2CO3 (2M in H2O; 3.5 eq.) and Pd(PPh3)4 (0.0 Seq.) in Tol:EtOH (1:1, 0.2M). The mixture was stirred at 80° C. for 12 h, cooled to rt, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as an oil. 1H NMR (400 MHz, acetone-d6): δ 8.82 (dd, 1H), 8.32 (dd, 1H), 7.99 (t, 1H), 7.81 (m, 2H), 7.75–7.66 (m, 4H), 7.55 (t, 1H), 7.5–7.45 (m, 3H), 7.36 (t, 1H), 3.21 (m, 1H), 1.39 (d, 6H).

Workup

  1. concentrationconcentrated
  2. stirringThe mixture was stirred at 80° C. for 12 h
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9d152d73f6d840d2939a9b079df5f676
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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