Sodium hydride → {3-Bromo-8-[(4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy]-6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]carbazol-5-yl}-acetic acid methyl ester

HRID 2275217Notes

Reaction equation

HRID 2275217 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:39])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]5[C@@H:27]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[O:26][C:25]([CH3:38])([CH3:37])[O:24]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.Br[CH2:41][C:42]([O:44][CH3:45])=[O:43].[H-].[Na+]>CN(C=O)C>[CH3:45][O:44][C:42](=[O:43])[CH2:41][N:12]1[C:11]2[C:10]([CH3:16])([CH3:15])[C:9]3[CH:17]=[C:18]([O:21][CH2:22][C@@H:23]4[C@@H:27]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[O:26][C:25]([CH3:38])([CH3:37])[O:24]4)[CH:19]=[CH:20][C:8]=3[C:7](=[O:39])[C:6]=2[C:5]2[C:13]1=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 66834604HCID 66834604, compound

Product 1

HCID 66834864{3-Bromo-8-[(4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy]-6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]carbazol-5-yl}-acetic acid methyl esterYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, 3-bromo-8-[(4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound T22-1, 40.0 mg, 65.2 μmol) was dissolved in DMF (0.20 mL), added at 0° C. with methyl bromoacetate (30.5 μL, 134.5 μmol) and sodium hydride (4.5 mg, 132 μmol), and then stirred at room temperature for 2 hr. The residues obtained from the reaction solution after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (44.5 mg, 85%).

Workup

  1. customThe residues obtained from the reaction solution
  2. concentrationafter concentration under reduced pressure
  3. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8fe33ae4423a469e980217fe009339a7
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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