Cesium carbonate → HCID 66748514, compound

HRID 1747964Notes

Reaction equation

HRID 1747964 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.CC1(C)C(C)(C)OB([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:28]4=[N:29][S:30](=[O:34])(=[O:33])[CH2:31][CH2:32][N:27]4[CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[C:28]3=[N:29][S:30](=[O:34])(=[O:33])[CH2:31][CH2:32][N:27]3[CH2:26][CH2:25][CH2:24]2)=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 676731-Fluoro-2-iodobenzeneHCID 66824090HCID 66824090, compound

Product 1

HCID 66748514HCID 66748514, compoundYield 1.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (18.0 mg) was added to a suspension of 1-fluoro-2-iodobenzene (69.0 mg), 9-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (60.0 mg) and cesium carbonate (152 mg) in toluene (3 mL) and EtOH (3 mL) and the mixture was stirred at 80° C. under nitrogen for 24 hr. Silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) and dissolved in THF (dry) (5 mL) and MeOH (5 mL) and platinum(IV) oxide (6.00 mg) was added and the mixture was stirred at room temperature under hydrogen for 2 days. The insoluble solid was removed by filtration through Celite-pad (eluted with EtOAc). Silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and crystallized from THF/IPE to give the title compound (0.80 mg) as colorless crystals.

Workup

  1. additionSilica-gel was added
  2. customthe volatiles were removed in vacuo
  3. customwas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)
  4. dissolutiondissolved in THF (dry) (5 mL)
  5. additionMeOH (5 mL) and platinum(IV) oxide (6.00 mg) was added
  6. stirringthe mixture was stirred at room temperature under hydrogen for 2 days
  7. customThe insoluble solid was removed by filtration through Celite-pad (eluted with EtOAc)
  8. additionSilica-gel was added
  9. customthe volatiles were removed in vacuo
  10. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  11. customcrystallized from THF/IPE

Sources & evidence

ORD record
ord-6faaf813331e461ea7a8a4332f668422
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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