Sodium hydride → [5-Carbamoyl-1-chlorocarbazol-4-yl]oxyacetic acid methyl ester

HRID 567362Notes

Reaction equation

HRID 567362 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:5]=1[C:6]1[C:7]([OH:18])=[CH:8][CH:9]=[C:10]([Cl:17])[C:11]=1[NH:12]2)(=[O:3])[NH2:2].[H-].[Na+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].[Cl-].[NH4+]>O1CCCC1>[CH3:26][O:25][C:23](=[O:24])[CH2:22][O:18][C:7]1[C:6]2[C:5]3[C:13](=[CH:14][CH:15]=[CH:16][C:4]=3[C:1](=[O:3])[NH2:2])[NH:12][C:11]=2[C:10]([Cl:17])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 227381395-Carbamoyl-4-hydroxy-1-chlorocarbazole

Product 1

HCID 69868854[5-Carbamoyl-1-chlorocarbazol-4-yl]oxyacetic acid methyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.28 g of 5-carbamoyl-4-hydroxy-1-chlorocarbazole in 6 ml of tetrahydrofuran was added to 0.043 g of sodium hydride (60% in mineral oil) in 1 ml of tetrahydrofuran and stirred for 60 minutes at room temperature. Methyl bromoacetate (0.11 ml) was then added and the reaction was stirred overnight. The reaction mixture was poured into 20 ml of saturated ammonium chloride solution and then extracted twice with ethyl acetate. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with chloroform and then 2:1 chloroform/ethyl acetate to afford 0.16 g (45%) of the subtitle compound. ESIMS m/e 333 (M++1), 335 (M++3), 331 (M+−1) NMR (300 MHz, d6-DMSO): δ 11.73 (s, 1H); 7.56 (d, J=8.1, 1H); 7.50 (br s, 1H); 7.43-7.35 (m, 2H); 7.18 (br s, 1H); 7.06 (d, J=7.8, 1H); 6.56 (d, J=8.6, 1H); 4.90 (s, 2H); 3.70 (s, 3H).

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialwith brine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-ab352053644949199ebccf4ae5280ebe
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

Loading…