Ethyl bromoacetate → HCID 18947548, compound

HRID 327231Notes

Reaction equation

HRID 327231 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:33][CH2:34][OH:35])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:41][C:42]([O:44]CC)=[O:43]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[C:8]2[CH2:33][CH2:34][O:35][CH2:41][C:42]([OH:44])=[O:43])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 18947557HCID 18947557, compound

Product 1

HCID 18947548HCID 18947548, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 91 mg of 2-[N-(p-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-ylmethoxy)indol-2-yl]ethanol from Step B in 2 mL THF at 0° C. under an argon atmosphere was added 40 mg of 80% sodium hydride over 30 min. Ethyl bromoacetate (0.3 ml) was added to the solution and the reaction stirred at RT overnight. The reaction was poured onto 10 mL of NH4OAc (25% solution), extracted with 3×10 mL of EtOAc, washed with 20 mL of H2O and dried over MgSO4. Removal of the solvent followed by column chromatography on silica gel afforded the ethyl ester of title compound. Hydrolysis of this ester under the conditions described in Step B of Example 1 provided the title compound, m.p. 185° C. (dec.).

Workup

  1. extractionextracted with 3×10 mL of EtOAc
  2. washwashed with 20 mL of H2O
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-3a1323ef83f74d75a69d14b40aa43f2b
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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