Propyne → (r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(5-methyl-isoxazol-3-yl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

HRID 545581Notes

Reaction equation

[CH:1]#[C:2][CH3:3].[F:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][C@@H:18]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([CH:28]=[N:29][OH:30])[CH:14]=2>C(Cl)Cl.[O-]Cl.[Na+]>[F:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][C@@H:18]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:28]1[CH:1]=[C:2]([CH3:3])[O:30][N:29]=1)[CH:14]=2

Participants

Conditions

Temperature: 23 °C

Procedure

Bubble propyne gas through a solution of (R)-cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Example 203) (0.065 g, 0.16 mmol) in methylene chloride and NaOCl solution maintained in a sealed tube. Cap the tube and stir at 23° C. for 16 h. Partition the reaction between methylene chloride and water. Separate and dry the organic portion over Na2SO4 to give 0.045 g of a tan solid. Purify by silca gel chromatography, eluting with 20-80% EtOAc/gradient to give an 0.030g (42%) of an off-white solid. mp: 190-192° C.; MS (ES): m/z 444 (M+1).

Workup

temperaturemaintained in a sealed tube
customCap the tube
customPartition
customthe reaction between methylene chloride and water
customSeparate
dry with materialdry the organic portion over Na2SO4

Sources & evidence

ORD record: ord-e242ecea617240a88b1166e9f019eb15
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935722B2

Reaction notes

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