Carbazole → HCID 67368093, compound

HRID 1615030Notes

Reaction equation

HRID 1615030 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][CH2:17][N:18]([CH2:31][CH3:32])[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29])(=[O:21])=[O:20].[H-].[Na+].CCCCCC.C(OCC)(=O)C>CN(C=O)C>[CH:10]1[C:11]2[N:12]([CH2:15][CH2:16][CH2:17][N:18]([CH2:31][CH3:32])[S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:28]([O-:30])=[O:29])(=[O:20])=[O:21])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 86660158HCID 86660158, compound

Product 1

HCID 67368093HCID 67368093, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carbazole (4.15 g, 24.8 mmol) and bromide 64 (9.7 g, 27.6 mmol) were dissolved in DMF (30 mL). NaH (2.0 g, 50.0 mmol, 2 eq) was added in portions, whereupon the temperature rose to 60° C. The reaction mixture was stirred for 1 h (TLC monitoring, hexane/ethyl acetate 3:2), poured into ice/water mixture, and extracted with ethyl acetate. The residue was triturated with ether. The yellow precipitate was filtered off and dried to afford 6.65 g (61%) of the product.

Workup

  1. customrose to 60° C
  2. extractionextracted with ethyl acetate
  3. customThe residue was triturated with ether
  4. filtrationThe yellow precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-9f5415440c3b416689fb29faee25aaaf
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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