Cesium fluoride → HCID 11375606, compound

HRID 1513855Notes

Reaction equation

HRID 1513855 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.[F:37][C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[C:42]([F:45])[C:43]=1[F:44].[F-].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:16][CH:15]=1)=[C:8]([C:40]1[CH:39]=[C:38]([F:37])[C:43]([F:44])=[C:42]([F:45])[CH:41]=1)[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 75806TricyclohexylphosphineHCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 116133766-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 11375606HCID 11375606, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Charge a flask with trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (800 mg, 1.52 mmol), 3,4,5-trifluorobenzene boronic acid (804 mg, 4.57 mmol) and cesium fluoride (1.1 g, 7.6 mmol) and purge with nitrogen. In a separate flask, charge palladium(II)acetate (34 mg, 0.15 mmol) and tricyclohexylphosphine (64 mg, 0.23 mmol) and purge with nitrogen. Add degassed acetonitrile and sonicate under nitrogen for 10 minutes. Add the catalyst solution to the solids and plunge into an 80° C. oil bath for 10 minutes. Cool to room temperature and filter through celite. Concentrate and redissolve in methylene chloride. Wash with saturated aqueous sodium bicarbonate, separate, dry, filter and concentrate. Purify the residue over silica gel, eluting with 0 to 5% methanol in methylene chloride, to yield 720 mg (93%) of the title compound: mass spectrum (ion spray) 508.3 (M+H).

Workup

  1. custompurge with nitrogen
  2. custompurge with nitrogen
  3. additionAdd
  4. customdegassed acetonitrile
  5. customsonicate under nitrogen for 10 minutes
  6. additionAdd the catalyst solution to the solids and plunge into an 80° C. oil bath for 10 minutes
  7. filtrationfilter through celite
  8. concentrationConcentrate
  9. dissolutionredissolve in methylene chloride
  10. washWash with saturated aqueous sodium bicarbonate
  11. customseparate
  12. customdry
  13. filtrationfilter
  14. concentrationconcentrate
  15. customPurify the residue over silica gel
  16. washeluting with 0 to 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-91e87b28af754794a86e49798bf8fb77
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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