Sodium Hydroxide → HCID 67624438, compound

HRID 726341Notes

Reaction equation

HRID 726341 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[C:10]1[CH2:9][CH2:8][CH:7]([N:25]([CH3:27])[CH3:26])[CH2:6][C:5]2=1.C([Li])(C)(C)C.CN(OC)[C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[OH-].[Na+]>O1CCCC1>[C:35]([C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([Si:15]([CH:19]([CH3:20])[CH3:21])([CH:16]([CH3:18])[CH3:17])[CH:22]([CH3:24])[CH3:23])[C:10]1[CH2:9][CH2:8][CH:7]([N:25]([CH3:26])[CH3:27])[CH2:6][C:5]2=1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:35]([C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([N:25]([CH3:26])[CH3:27])[CH2:6][C:5]2=1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 569575N-Methoxy-N-methylbenzamideHCID 15512574HCID 15512574, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 67624438HCID 67624438, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.50 gm (1.11 mMol) 6-bromo-3-(dimethyl)amino-9-triisopropylsilyl-1,2,3,4-tetrahydro-9H-carbazole in 50 mL tetrahydrofuran at -78° C. were added 1.96 mL (3.33 mMol) t-butyllithium (1.7M in pentane) and the resulting dark solution was allowed to stir for 30 minutes. To this mixture were then added 0.20 gm (1.22 mMol) N-methyl-N-methoxybenzamide and the reaction mixture was allowed to warm to room temperature over 1 hour. The reaction mixture was then treated with 0.1N sodium hydroxide and then extracted well with chloroform. The organic phases were combined, dried over potassium carbonate and concentrated under reduced pressure to give 0.48 gm (91%) of the desired compound as a red-orange oil.

Workup

  1. extractionextracted well with chloroform
  2. dry with materialdried over potassium carbonate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa48570583fc471d8a1a175aba07b791
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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