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Sodium Carbonate → N-[5-(2,4-difluorophenyl)-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamide

HRID 78461
Notes
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Reaction equation

HRID 78461 reaction equation
Cl[C:2]1[S:6][C:5](=[N:7][C:8](=[O:10])[CH3:9])[N:4]([CH2:11][CH2:12][O:13][CH3:14])[CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C(O)C.C(OCC)(=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>[F:15][C:16]1[CH:17]=[C:18]([F:22])[CH:19]=[CH:20][C:21]=1[C:2]1[S:6][C:5](=[N:7][C:8](=[O:10])[CH3:9])[N:4]([CH2:11][CH2:12][O:13][CH3:14])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343362,6-Difluorophenylboronic acidHCID 66858991N-[5-chloro-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamide

Product 1

HCID 66860261N-[5-(2,4-difluorophenyl)-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamideYield 86.4%

Reagents, catalysts & solvents 3

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
85 °C

Procedure

A flask was charged with the product from Example 197A (10.2 g, 42.6 mmol), 2,6-difluorophenylboronic acid (8.08 g, 51.1 mmol), Na2CO3 (64.0 mL of a 2 M aqueous solution, 128 mmol) and PdCl2(PPh3)2 (1.5 g, 2.13 mmol) in 100 mL of DME/H2O/ethanol (7:3:2). The mixture was warmed to 85° C. and stirred overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate: hexane to provide 11.5 g (86%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 2.17 (s, 3H) 3.27 (s, 3H) 3.71 (t, J=5.3 Hz, 2H) 4.37 (t, J=5.4 Hz, 2H) 7.17-7.24 (m, 1H) 7.38-7.48 (m, 1H) 7.64-7.74 (m, 1H) 7.88 (s, 1H); MS (ES I+) m/z 313 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate

Sources & evidence

ORD record
ord-2f1b77648d8e44ca99e945dcd8e4928a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841334B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes