Sodium hydride → HCID 10340981, compound

HRID 2293603Notes

Reaction equation

HRID 2293603 reaction equation
BrC1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:3]=1[C:20]([O:22]CC)=[O:21].BrC1C2C(=CC=CC=2)NC=1C(OCC)=[O:36].[CH3:40][O:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Cl)=[CH:44][CH:43]=1.[H-].[Na+]>CN(P(N(C)C)(N(C)C)=O)C>[CH2:40]1[O:41][C:42]2[CH:49]=[CH:48][C:45]([C:46]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]([CH2:11][C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=4)[C:3]=3[C:20]([OH:22])=[O:21])=[CH:44][C:43]=2[O:36]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 4715017Ethyl 3-Bromoindole-2-carboxylateHCID 21476954HCID 21476954, compound

Product 1

HCID 10340981HCID 10340981, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

Ethyl 3-bromo-1-(4-methoxybenzyl)indole-2-carboxylate. To a solution of ethyl 3-bromoindole-2-carboxylate (2.0 g, 7.46 mmol) and 4-methoxybenzyl chloride (7.46 mmol) in HMPA (5 mL) was added a slurry of NaH (240 mg of 80% oil dispersion, oil removed by pentane washing, 8.0 mmol) in HMPA (1 mL). After 30 min at room temperature the reaction mixture was partitioned between 3N HCl (100 mL) and EtOAc (150 mL). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O, saturated aqueous NaCl and dried (Na2SO4). The solvent was removed in vacuo to afford the title compound (2.55 g, 88%) which was used in the next step without further purification.

Workup

  1. customAfter 30 min at room temperature the reaction mixture was partitioned between 3N HCl (100 mL) and EtOAc (150 mL)
  2. extractionThe organic extract
  3. washwas washed successively with H2O, aqueous NaHCO3, H2O, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0f0a63c6a9874c81a4d615a119da6e77
Source dataset
uspto-grants-1997_11
Patent number
US05686481

Reaction notes

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