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Cesium carbonate → 2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)-5-(thiazol-4-yl)furan-3(2H)-one

HRID 1258363
Notes
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Reaction equation

HRID 1258363 reaction equation
Br[C:2]1[C:3](=[O:14])[C:4]([CH3:13])([CH3:12])[O:5][C:6]=1[C:7]1[N:8]=[CH:9][S:10][CH:11]=1.CC1(C)C(C)(C)OB([C:23]2[CH:40]=[CH:39][C:26]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:25][CH:24]=2)O1.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]>[CH3:12][C:4]1([CH3:13])[C:3](=[O:14])[C:2]([C:23]2[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:39][CH:40]=2)=[C:6]([C:7]2[N:8]=[CH:9][S:10][CH:11]=2)[O:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 583680032-((4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)quinolineHCID 593548524-bromo-2,2-dimethyl-5-(thiazol-4-yl)furan-3(2H)-one

Product 1

HCID 593547932,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)-5-(thiazol-4-yl)furan-3(2H)-oneYield 18.9%

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-(thiazol-4-yl)furan-3(2H)-one (0.1 g, 0.37 mmol), 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)quinoline (0.164 g, 0.454 mmol), and Cs2CO3 (0.673 g, 2.06 mmol) in toluene (1 mL) and water (1 mL) was degassed and Pd(dppf)Cl2 (0.067 g, 0.082 mmol) was added under an inert atmosphere, and degassed once more. Then the reaction was refluxed for 2 h and was filtered through a pad of Celite®, the filtrate was diluted with EtOAc (10 mL), washed with water (5 mL), brine (5 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 2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)-5-(thiazol-4-yl)furan-3(2H)-one (30 mg, 18%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 9.17 (s, 1H), 8.43 (d, J=8.5 Hz, 1 H), 8.30 (s, 1 H), 8.02-7.98 (m, 2 H), 7.80 (t, J=8.2 Hz, 1 H), 7.70 (d, J=8.2 Hz, 1 H), 7.62 (t, J=8.5 Hz, 1 H), 7.24 (d, J=7.5 Hz, 2 H), 7.08 (d, J=7.4 Hz, 2 H), 5.38 (s, 2 H), 1.42 (s, 6 H). MS: [M+H]: m/z=429.1. HPLC: 97.9% (RT-2.36 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 once more
  3. temperatureThen the reaction was refluxed for 2 h
  4. filtrationwas filtered through a pad of Celite®
  5. additionthe filtrate was diluted with EtOAc (10 mL)
  6. washwashed with water (5 mL), brine (5 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-f258a6b227484c8b98ff9c1ae3d94c6a
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466148B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes