Methanol → HCID 21949971, compound

HRID 2215829Notes

Reaction equation

[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C(Cl)Cl.[CH2:10]([O:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[CH:15][CH:14]=1)[CH3:11].[CH3:22][O-:23].[Na+].CO>CCOCC>[CH2:10]([O:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([C:1](=[O:5])[C:2]([O:23][CH3:22])=[O:3])=[CH:18][NH:19]2)=[CH:15][CH:14]=1)[CH3:11]

Participants

Conditions

Temperature: 4 °C

Procedure

A 2.0 M solution of oxalyl chloride in methylene chloride (6.65 mL, 13.3 mmol) was added to a solution of 6-ethoxyindole (2.0 g, 12.4 mmol) in ether (25 mL) dropwise over 10 min at 4° C. under N2. The resulting mixture was stirred for 1 h at 4° C. A 25% (w/w) sodium methoxide in methanol solution (6.2 mL, 28.5 mmol) was added at −78° C. The mixture was allowed to warm up to room temperature and stirred for 4 h. The reaction was quenched with water (50 mL) and extracted with methylene chloride. The organic solution was dried (MgSO4) and concentrated at reduced pressure. The residue was stirred in a solution of EtOAc (50 mL) and ether (50 mL) for 10 min. Solid was collected by filtration to give the title compound (2.2 g, 73%) after drying. 1H NR (CDCl3) δ 8.20 (s, 1H), 7.90 (d, J=9 Hz, 1H), 6.92 (s, 1H), 6.82 (d, J=9 Hz, 1H), 4.00 (q, J=6.5 Hz, 2H), 3.78 (s, 3H), 1.30 (t, J=6.5 Hz, 3H)

Workup

temperatureto warm up to room temperature
stirringstirred for 4 h
customThe reaction was quenched with water (50 mL)
extractionextracted with methylene chloride
dry with materialThe organic solution was dried (MgSO4)
concentrationconcentrated at reduced pressure
stirringThe residue was stirred in a solution of EtOAc (50 mL) and ether (50 mL) for 10 min
filtrationSolid was collected by filtration

Sources & evidence

ORD record: ord-badce16af68f4a2f86579ea238f3b4fd
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109229B2

Reaction notes

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