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Potassium Carbonate → 4-(4-Methoxybenzyloxy)-8-chloro-7-methoxy-2-(4-methylthiazol-2-yl)quinoline

HRID 388700
Notes
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Reaction equation

HRID 388700 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[C:14]([Cl:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]=[C:11](Cl)[CH:10]=2)=[CH:5][CH:4]=1.C([Sn](CCCC)(CCCC)[C:30]1[S:31][CH:32]=[C:33]([CH3:35])[N:34]=1)CCC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[C:14]([Cl:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]=[C:11]([C:30]3[S:31][CH:32]=[C:33]([CH3:35])[N:34]=3)[CH:10]=2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazoleHCID 566051532,8-Dichloro-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline

Product 1

HCID 578167174-(4-Methoxybenzyloxy)-8-chloro-7-methoxy-2-(4-methylthiazol-2-yl)quinolineYield 65%

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of compound 274 (1 g, 1 eq.) and 2-(tributylstannyl)-4-methylthiazole (1.28 g, 1.2 eq.) in DMF (14 mL) were added PdCl2(PPh3)2 (193 mg, 10%) and potassium carbonate (455 mg, 1.2 eq.) and the resulting mixture was stirred at 90° C. overnight. DMF was concentrated under vacuum and water and dichloromethane were added. The aqueous layer was extracted with dichloromethane and the combined organic layers washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on a silica gel to yield compound 275 as a white solid in 65% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.57 (s, 3H), 3.86 (s, 3H), 4.06 (s, 3H), 5.33 (s, 2H), 6.98 (d, J=8.64 Hz, 2H), 7.08 (s, 1H), 7.25 (d, J=9.25 Hz, 1H), 7.46 (d, J=8.64 Hz, 2H), 7.74 (s, 1H), 8.12 (d, J=9.25 Hz, 1H); MS (ESI, EI+): m/z=427.1 (MH+).

Workup

  1. concentrationDMF was concentrated under vacuum and water and dichloromethane
  2. additionwere added
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washthe combined organic layers washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on a silica gel

Sources & evidence

ORD record
ord-e2709501c34742fa94b80b2298814654
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377962B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes