Potassium Phosphate, Tribasic → HCID 131733006, compound

HRID 2177602Notes

Reaction equation

HRID 2177602 reaction equation
FC(F)(F)S(O[C:7]1[C:15]2[CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=2[N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:8]=1)(=O)=O.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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].Cl[Pd]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]>[C:33]1([C:7]2[C:15]3[CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=3[N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:28])[CH3:29])[N:8]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 90409916HCID 90409916, compound

Product 1

HCID 131733006HCID 131733006, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of tert-butyl 3-(((trifluoromethyl)sulfonyl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate (440 mg, 0.88 mmol) in 1,4-dioxane (9 mL) was added phenylboronic acid (331 mg, 2.63 mmol), potassium phosphate (559 mg, 2.63 mmol), 1,1′-bis(diphenylphosphino)ferrocene-dichloropalladium (II) (32 mg, 0.05 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (10 mg, 0.02 mmol). The reaction was stirred at 160° C. for 1 hour in a microwave reactor. The reaction was cooled to rt and filtered through Celite© and rinsed with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. The residue was purified via chromatography on silica gel (0-25% ethyl acetatehexanes) to provide the desired product (298 mg, 79%). MS (ESI) mass calcd. C23H35N3O3Si 429.7. m/z found, 430.2 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered through Celite©
  3. washrinsed with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via chromatography on silica gel (0-25% ethyl acetatehexanes)

Sources & evidence

ORD record
ord-6be51ca0293d4de48bd69df86c9bad0a
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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