(r)-Cyclopropanecarboxylic acid[6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]amide → Cyclopropanecarboxylic acid[6-cyano-9-(6-fluoro-pyridin-2-ylmethyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

HRID 545573Notes

Reaction equation

HRID 545573 reaction equation
C[N:2](CCO)C.CCO.[C:10]([C:12]1[CH:13]=[C:14]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])C=1)[C:20]1[CH2:19][CH2:18][C@@H:17]([NH:33][C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])[CH2:16][C:15]2=1)#[N:11]>>[C:10]([C:12]1[CH:13]=[C:14]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:2]=1)[C:20]1[CH2:19][CH2:18][CH:17]([NH:33][C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])[CH2:16][C:15]2=1)#[N:11]

Participants

3

Reactant 2

HCID 59161284(r)-Cyclopropanecarboxylic acid[6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]amideHCID 87410002DMEA EtOH

Product 1

HCID 67198529Cyclopropanecarboxylic acid[6-cyano-9-(6-fluoro-pyridin-2-ylmethyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

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).

Workup

  1. washto elute
  2. filtrationfilter

Sources & evidence

ORD record
ord-689e8710e4904f4a994091bb81f46dd1
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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