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Cesium carbonate → 4-(4-((6-fluoroquinolin-2-yl)methoxy)phenyl)-2,2-dimethyl-5-(pyridin-4-yl) furan-3(2H)-one

HRID 1425887
Notes
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Reaction equation

HRID 1425887 reaction equation
Br[C:2]1[C:3](=[O:15])[C:4]([CH3:14])([CH3:13])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=1)[CH:21]=[CH:20]2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.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]>[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([CH2:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]3[C:3](=[O:15])[C:4]([CH3:14])([CH3:13])[O:5][C:6]=3[C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)=[CH:33][CH:34]=1)[CH:21]=[CH:20]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 593547756-Fluoro-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)quinolineHCID 593548244-bromo-2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one

Product 1

HCID 593548234-(4-((6-fluoroquinolin-2-yl)methoxy)phenyl)-2,2-dimethyl-5-(pyridin-4-yl) furan-3(2H)-oneYield 25%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2,2-dimethyl-5-(pyridin-4-yl) furan-3(2H)-one (0.085 g, 0.32 mmol), 6-Fluoro-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)quinoline (0.12 g, 0.32 mmol), and Cs2CO3 (0.52 g, 1.58 mmol) in toluene (5 mL) and water (2 mL) was degassed, added Pd(dppf)Cl2 (0.052 g, 0.06 mmol) under an inert atmosphere and degassed again. Then the reaction was refluxed for 2 h. The reaction mixture was filtered through a pad of Celite®, the filtrate was diluted with EtOAc (30 mL), washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-(4-((6-fluoroquinolin-2-yl)methoxy)phenyl)-2,2-dimethyl-5-(pyridin-4-yl) furan-3(2H)-one (35 mg, 25%) as a pale yellow solid. 1H NMR (500 MHz, do-DMSO): δ 8.71 (d, J=8.5 Hz, 2H), 8.42 (t, J=7.9 Hz, 1H), 8.1 (t, J=8.4 Hz, 1H), 7.70-7.61 (m, 3H), 7.44 (d, J=8.5 Hz, 2H), 7.18 (d, J=7.4 Hz, 2H), 7.11 (d, J=7.5 Hz, 2H), 5.40 (s, 2H), 1.44 (s, 6H). MS: [M+H]: m/z=441.1. HPLC: 90.1% (RT-2.39 min), Column: Acquity BEH-C-18, 50×2.1 mm, 1.7 um. Mobile Phase: 0.025% TFA in Water (A), ACN (B), Flow rate: 0.5 ml/min (Gradient).

Workup

  1. customwas degassed
  2. customdegassed again
  3. temperatureThen the reaction was refluxed for 2 h
  4. filtrationThe reaction mixture was filtered through a pad of Celite®
  5. additionthe filtrate was diluted with EtOAc (30 mL)
  6. washwashed with water (20 mL), brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto obtain the crude product
  11. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-a248f05d63a74d07be1a975d1838b453
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933074B2

Reaction notes

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