Sodium hydride → HCID 9915979, compound

HRID 555316Notes

Reaction equation

HRID 555316 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH:30]2[CH2:32][O:31]2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[H-].[Na+]>>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH2:25][N:26]([CH2:29][CH:30]([OH:31])[CH2:32][N:6]2[C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=3)[CH2:27][CH2:28]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2748743,6-DibromocarbazoleHCID 15491146tert-Butyl 4-[(oxiran-2-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 9915979HCID 9915979, compoundYield 72%

Procedure

The same method as employed in the preparation of Example 1 but starting from 3,6-dibromo-9H-carbazole, (±)-4-oxiranylmethyl-piperazine-1-carboxylic acid tert-butyl ester and sodium hydride gives after flash chromatography the title compound as a white foam in a 72% yield. M.p: 90-95° C.

Workup

  1. customThe same method as employed in the preparation of Example 1

Sources & evidence

ORD record
ord-3e5a6e250c4f4bd89c2670f7eb3edd35
Source dataset
uspto-grants-2011_11
Patent number
US08053436B1

Reaction notes

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