Methanol → HCID 16762498, compound

HRID 2215821Notes

Reaction equation

HRID 2215821 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C(Cl)Cl.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2.[CH3:20][O-:21].[Na+].CO>CCOCC>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:1](=[O:5])[C:2]([O:21][CH3:20])=[O:3]

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 678615-FluoroindoleHCID 10942334Sodium Methoxide

Product 1

HCID 16762498HCID 16762498, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 2.0 M solution of oxalyl chloride in methylene chloride (4.50 mL, 9.0 mmol) was added to a solution of 5-fluoroindole (1.14 g, 8.4 mmol) in ether (19 mL) dropwise over 10 min at 4° C. under N2. The ice bath was removed and the resulting mixture was stirred for 2 h. A 25% sodium methoxide in methanol solution (4.3 mL, 18.8 mmol) was added at −78° C. over 5 min. The mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction was quenched with water (50 mL), filtered and rinsed with cold ether to afford the title compound (1.34, 72%) as a yellow solid. 1H NMR (DMSO-d6) δ 12.51 (bs, 1H), 8.56 (s, 1H), 7.86 (m, 1H), 7.60 (m, 1H), 7.15 (m, 1H), 3.90 (s, 3H).

Workup

  1. customThe ice bath was removed
  2. stirringstirred for 1 h
  3. customThe reaction was quenched with water (50 mL)
  4. filtrationfiltered
  5. washrinsed with cold ether

Sources & evidence

ORD record
ord-20b4bb0cd6d642ef9af1053a2278ed71
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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