Methanol → HCID 10633084, compound

HRID 2215817Notes

Reaction equation

HRID 2215817 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:12](Cl)(=[O:16])[C:13](Cl)=[O:14].C(Cl)Cl.[CH3:21][O-:22].[Na+].CO>C(OCC)C>[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[C:3]2[C:12](=[O:16])[C:13]([O:22][CH3:21])=[O:14])#[N:11]

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 27513Indole-5-carbonitrileHCID 65578Oxalyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 10633084HCID 10633084, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1H-indole-5-carbonitrile (1.14 g, 8.04 mmol) in diethyl ether (12 mL) at 4° C. was added a 2.0 M solution of oxalyl chloride in methylene chloride (4.2 mL, 8.4 mmol). The resulting solution was allowed to warm to room temperature. After 90 min, the solution was cooled to −78° C. To this solution was added 25% (w/w) solution of sodium methoxide in methanol (3.83 mL, 16.8 mmol). The resulting solution was allowed to warm to room temperature. After one hour, the solution was filtered to give the title compound (768 mg, 42%) as a light brown solid. 1H NMR (DMSO-d6) δ 9.39 (s, 1H), 8.67 (m, 1H), 8.50 (s, 1H), 7.29 (m, 1H), 3.87 (s, 3H).

Workup

  1. temperaturethe solution was cooled to −78° C
  2. temperatureto warm to room temperature
  3. waitAfter one hour
  4. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-c4c870643d4344a28c56a661c9647410
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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