Dimethylformamide → 2-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].C[Li].C([Li])(C)(C)C.CN(C)[CH:32]=[O:33]>O1CCCC1.C(OCC)C.CCCCC>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([CH:32]=[O:33])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
A solution of 5-bromo-2-chloro-N-(tricyclo[3.3.1.13.7]dec-1-ylmethyl)-benzamide (3.25 g, Example 1a) in tetrahydrofuran (150 ml) was cooled to −78° C. under a nitrogen atmosphere. A solution of 1.4M methyllithium in diethyl ether (6.1 ml) was added to this solution over 2 min. The mixture was stirred at −78° C. for 10 min., then a 1.7M solution of tert-butyllithium in pentane (10.0 ml) was added dropwise. The mixture was stirred at −78° C. for a further 10 min., then dimethylformamide (1.0 ml) was added. The resulting solution was stirred at −78° C. for 30 min., quenched with saturated aqueous ammonium chloride solution (100 ml) and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give the subtitled compound as a solid (2.76 g).
Workup
- stirringThe mixture was stirred at −78° C. for a further 10 min.
- stirringThe resulting solution was stirred at −78° C. for 30 min.
- customquenched with saturated aqueous ammonium chloride solution (100 ml)
- extractionextracted with ethyl acetate
- dry with materialThe combined extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationthe filtrate concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a35cf2491b0a4b7eb9ef11e9e11288eb
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881754B2
Reaction notes
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