Water → HCID 178422165, compound

HRID 2095742Notes

Reaction equation

HRID 2095742 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH3:20])=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F-].[K+].[C:32]1([S:38]([C:41]([S:63]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)(=[O:65])=[O:64])([F:62])[CH:42]([C:52]2[C:60]3[C:55](=[N:56][CH:57]=[C:58](Br)[CH:59]=3)[NH:54][CH:53]=2)[C:43]2[C:48]([Cl:49])=[CH:47][CH:46]=[C:45]([F:50])[C:44]=2[Cl:51])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O1CCOCC1.O>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH3:20])=[C:18]([C:58]3[CH:59]=[C:60]4[C:52]([CH:42]([C:43]5[C:48]([Cl:49])=[CH:47][CH:46]=[C:45]([F:50])[C:44]=5[Cl:51])[C:41]([F:62])([S:63]([C:66]5[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=5)(=[O:64])=[O:65])[S:38]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)(=[O:39])=[O:40])=[CH:53][NH:54][C:55]4=[N:56][CH:57]=3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 962WaterHCID 312751,4-DioxaneHCID 522689Potassium FluorideHCID 866593275-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridineHCID 178421688HCID 178421688, compound

Product 1

HCID 178422165HCID 178422165, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
90 °C

Procedure

To a mixture of 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (202.16 mg, 0.48079 mmol), Potassium fluoride (76.18 mg, 1.311 mmol) and 3-[2,2-Bis-benzenesulfonyl-1-(2,6-dichloro-3-fluoro-phenyl)-2-fluoroethyl]-5-bromo-1H-pyrrolo[2,3-b]pyridine (300.00 mg, 0.43708 mmol) in 1,4-Dioxane (10.00 mL, 128.1 mmol) and H2O (2.500 mL, 138.8 mmol) was added (1,1′-bis-(diphenylphosphino)-ferrocene) palladium dichloride (15.99 mg, 0.02185 mmol) under Nitrogen atmosphere, the resulting mixture was then stirred at 90° C. for 90 min. Then the solvent was removed under reduced pressure to give a residue, which was purified by silica gel chromatography (eluent: 20-30% AcOEt in DCM) to give the title compound. MS (ES+): m/z 899.20, 901.21 [MH+]. HPLC: tR=1.98 min (polar—3 min, TOF).

Workup

  1. customThen the solvent was removed under reduced pressure
  2. customto give a residue, which
  3. customwas purified by silica gel chromatography (eluent: 20-30% AcOEt in DCM)

Sources & evidence

ORD record
ord-64f1a9f22683448f881c246cc3da9ba0
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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