Dimethylformamide → HCID 12192482, compound

HRID 2117966Notes

Reaction equation

HRID 2117966 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12](=[O:25])[C:13]3[C:17]=2[C:16](=[O:18])[NH:15][C:14]=3[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(C1C=CC(C)=CC=1)(O[CH3:30])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:30][N:15]1[C:16](=[O:18])[C:17]2=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[O:11][C:12](=[O:25])[C:13]2=[C:14]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 178517440HCID 178517440, compound

Product 1

HCID 12192482HCID 12192482, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of furopyrrole 12 (0.9 g, 2.7 mmol), methyl tosylate (750 mg, 4.04 mmol), potassium carbonate (1 g, 7.2 mmol) and dimethyl formamide was stirred at room temperature overnight. Water was then added, and the organic component extracted with DCM. The solvent was removed, and washing with water then methanol gave the methylated compound 13 as a red solid (0.652 g, 70%), m.p. 253-255° C. δH (CDCl3) 8.55 and 8.38 (4H, AA′BB′, Ar), 7.88-7.84 (2H, m, o-Ph), 7.65-7.60 (3H, m, m/p-Ph) and 3.49 (3H, s, NCH3). λmax (abs) (DCM)/nm 482 ( 17,462)

Workup

  1. extractionthe organic component extracted with DCM
  2. customThe solvent was removed
  3. washwashing with water

Sources & evidence

ORD record
ord-f06a91a029f849b58719f4197a7911a2
Source dataset
uspto-grants-2008_10
Patent number
US07442804B2

Reaction notes

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