Sodium Carbonate → HCID 11521890, compound

HRID 1020319Notes

Reaction equation

HRID 1020319 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(NC(=O)[O-])(C)(C)C.Cl[C:46]1[CH:57]=[CH:56][C:55]2[CH:51]3[CH2:52][NH:53][CH2:54][CH:50]3[CH2:49][C:48]=2[CH:47]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:46]1[CH:57]=[CH:56][C:55]2[CH:51]3[CH2:52][NH:53][CH2:54][CH:50]3[CH2:49][C:48]=2[CH:47]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343362,6-Difluorophenylboronic acidHCID 86602853HCID 86602853, compound

Product 1

HCID 11521890HCID 11521890, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Triphenylphosphine (2 mg), palladium(II) acetate (1 mg), 2,6-difluorophenyl boronic acid (20 mg, 0.12 mmol), and aqueous sodium carbonate (0.15 mL, 0.3 mmol) were added to a solution of (N-tert-butylcarbamate-6-chloro-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 11, Step F) (30 mg, 0.1 mmol) in acetonitrile (1 mL), and stirred for 24 h at 80° C. The reaction mixture was concentrated, diluted with EtOAc (5 mL) and washed with H2O (5 mL). The organic extract was dried over MgSO4 and concentrated to give the subtitle compound, which was used without further purification. MS calculated for C22H23F2NO2+H: 372, observed: 372.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (5 mL)
  3. washwashed with H2O (5 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-827f75e544b9415e9484fb0ad6466c53
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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