Sodium Carbonate → HCID 86602852, compound
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:37]([NH:41][C:42](=[O:44])[O-:43])([CH3:40])([CH3:39])[CH3:38].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>[C:37]([NH:41][C:42](=[O:43])[O-:44])([CH3:40])([CH3:39])[CH3:38].[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]=1Participants
7
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
- concentrationThe reaction mixture was concentrated
- additiondiluted with EtOAc (5 mL)
- washwashed with H2O (5 mL)
- extractionThe organic extract
- dry with materialwas dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8c4cccac2c88465c8353beb1c717bb23
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232311B2
Reaction notes
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