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Cesium carbonate → HCID 178493340, compound

HRID 724304
Notes
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Reaction equation

HRID 724304 reaction equation
Cl[C:2]1[N:17]=[CH:16][C:15]([F:18])=[CH:14][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1)=[O:5].[CH3:19][S:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[O:28][CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:18][C:15]1[CH:16]=[N:17][C:2]([O:27][C:24]2[CH:25]=[CH:26][C:21]([S:20][CH3:19])=[C:22]([O:28][CH3:29])[CH:23]=2)=[C:3]([CH:14]=1)[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1)=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 218771303-Methoxy-4-(methylsulfanyl)phenolHCID 178523807HCID 178523807, compound

Product 1

HCID 178493340HCID 178493340, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

2-Chloro-5-fluoro-N-(trans-4-hydroxy-cyclohexyl)-nicotinamide (150 mg, 0.55 mmol), 4-methylsulfanyl-3-methoxy-phenol (94 mg, 0.55 mmol) and caesium carbonate (358 mg, 1.10 mmol) were suspended in DMF (2 ml) and the reaction was heated to 55° C. and stirred at this temperature under nitrogen for 18 h. The reaction was quenched with sat. ammonium chloride solution (1.5 ml) and water (1.5 ml) and the organic phase was collected by passing the mixture through a Chemelute™ cartridge, washing with ethyl acetate. The solvent was removed on a Genevac™ and the residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (100:0 changing to 96:4, by volume) to give 5-fluoro-N-(trans-4-hydroxy-cyclohexyl)-2-(4-methylsulfanyl-3-methoxy-phenoxy)-nicotinamide (99 mg) as an off-white foam.

Workup

  1. customThe reaction was quenched with sat. ammonium chloride solution (1.5 ml) and water (1.5 ml)
  2. customthe organic phase was collected
  3. washwashing with ethyl acetate
  4. customThe solvent was removed on a Genevac™
  5. customthe residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (100:0 changing to 96:4, by volume)

Sources & evidence

ORD record
ord-372580d490c24c16be384060f5964a70
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07141586B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes