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

HRID 51449Notes

Reaction equation

HRID 51449 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): δ11.73 (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-1c723bde251a477d803add452f1b68b2
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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