2-Fluoro-5-iodopyridine → HCID 16748705, compound
Reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[F:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][N:17]=1.COC1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)C>[F:15][C:16]1[N:17]=[CH:18][C:19]([N:5]2[CH2:6][C@@H:1]3[CH2:7][C@H:4]2[CH2:3][N:2]3[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:20][CH:21]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.300 g, 1.01 mmol), prepared as described in (J. Med. Chem., (1988) 31, 1598-1611), in anhydrous toluene (30 ml) was treated with 2-fluoro-5-iodopyridine (0.34 g, 1.52 mmol), available as described in (U.S. Pat. No. 5,733,912), Pd2(dba)3 (0.028 g, 0.03 mmol), (S)-(−)-2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl (0.028 g, 0.06 mmol), available from Strem Chemicals, and sodium tert-butoxide (0.248 g, 2.58 mmol). The reaction mixture was heated at 80° C. for 5 hours. The reaction mixture was poured into diethyl ether (100 mL), washed with brine (100 ml), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 (3% MeOH/CH2Cl2) to provide the title compound (0.095 g, 21% yield) as a yellow oil. MS (DCI/NH3) m/z 276 (M+H)+.
Workup
- washwashed with brine (100 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe residue was purified by chromatography on SiO2 (3% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-c3c6d36e5c3c445fa8d85a05b0fad08c
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265115B2
Reaction notes
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