Potassium Phosphate, Tribasic → HCID 57941474, compound

HRID 1437952Notes

Reaction equation

HRID 1437952 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:16](=[O:17])[C:15]3[C@@H:14]4[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]4)[C:10]=3[N:9]2[CH3:22])[CH:5]=[CH:6][CH:7]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:16](=[O:17])[C:15]3[C@@H:14]4[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]4)[C:10]=3[N:9]2[CH3:22])[CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 57941452HCID 57941452, compound

Product 1

HCID 57941474HCID 57941474, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A degassed mixture of 2-(3-bromo-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Example 22; 75 mg, 0.2 mmol), phenyl-boronic acid (38 mg, 0.3 mmol), potassium phosphate (132 mg, 0.62 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17 mg, 0.024 mmol) in dimethoxyethane (3 mL) was sealed under argon and heated at 80 degrees overnight and then at 60 degrees over the weekend. The reaction mixture was filtered and the residue was washed with dimethoxyethane. The solvent was evaporated from the filtrate and the residue was purified by chromatography on a Sep-Pak column, eluting with 15% ethyl acetate/hexanes to give (4S,7R)-2-biphenyl-3-yl-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (13 mg, 17%) as a white solid. ES(+)-MS (M+H) 359.

Workup

  1. customwas sealed under argon
  2. temperatureheated at 80 degrees overnight
  3. customat 60 degrees
  4. filtrationThe reaction mixture was filtered
  5. washthe residue was washed with dimethoxyethane
  6. customThe solvent was evaporated from the filtrate
  7. customthe residue was purified by chromatography on a Sep-Pak column
  8. washeluting with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-14027102211f45dca27d915f4ee7b28e
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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