2-(Bromomethyl)-6-fluoropyridine → Cyclopropanecarboxylic acid[6-cyano-9-(6-fluoro-pyridin-2-ylmethyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH2:10][CH2:9][CH:8]([NH:16][C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH2:7][C:6]2=1)#[N:2].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[N:25]=1>>[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[N:25]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH:16][C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH2:7][C:6]2=1)#[N:2]Participants
3
Procedure
Prepare the title compound from cyclopropanecarboxylic acid(6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)amide (Preparation 69) (10.0 g, 35.8 mmol) and 2-bromomethyl-6-fluoro-pyridine (Preparation 44) (7.49 g, 39.4 mmol) by essentially following procedures as described in Preparation 45 to obtain 4.30 g (31%) of a salmon colored solid. Resolve the enantiomers using chiral chromatography essentially as described for Example 194, but using 0.2% DMEA/EtOH eluent. (R)-Isomer is first to elute. Slurry the solid in EtOAc and filter to give the title compound. m.p.=243-245° C.; MS (ES): m/z 389 (M+1).
Sources & evidence
- ORD record
- ord-f8a5a72cec3040ac9cfbda0235cc11e6
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935722B2
Reaction notes
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