Sodium Carbonate → HCID 68563385, compound

HRID 2108495Notes

Reaction equation

HRID 2108495 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.P(Cl)(Cl)(Cl)=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[CH:20]=2)[CH:15]=[CH:14]1.C([O-])([O-])=O.[Na+].[Na+]>ClCCCl.O>[CH3:25][O:24][C:22]([C:19]1[CH:20]=[C:21]2[C:16](/[C:15](=[C:3]3/[N:2]([CH3:1])[CH2:6][CH2:5][CH2:4]/3)/[CH:14]=[N:13]2)=[CH:17][CH:18]=1)=[O:23]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidone2×HCID 24813Phosphorus oxychlorideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 68563385HCID 68563385, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 1.6 mL (16 mmol) 1-methyl-2-pyrrolidone and 10 mL phosphoryl chloride (POCl3) in 10 mL 1,2-dichloroethane was stirred for 15 min and 1.75 g (10 mmol) methyl indole-6-carboxylate and 1.6 mL (16 mmol) 1-methyl-2-pyrrolidone in 10 mL 1,2-dichloroethane was added. The mixture was heated to reflux for 2 h. Water and Na2CO3 aq. was added to adjust to pH=9. Subsequently the mixture was extracted with DCM and the combined organic layers were washed with water, dried with Na2SO4 and evaporated to dryness. Trituration with acetone provided 1.45 g (57%) of the title compound as light brown solid. MS (m/e): 257.2 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. extractionSubsequently the mixture was extracted with DCM
  4. washthe combined organic layers were washed with water
  5. dry with materialdried with Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-89ffc99f4e574f37b7b7dc2320824e5e
Source dataset
uspto-grants-2009_04
Patent number
US07514433B2

Reaction notes

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