Dimethylformamide → HCID 12192481, compound

HRID 2117963Notes

Reaction equation

HRID 2117963 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10](=[O:23])[C:11]3[C:15]=2[C:14](=[O:16])[NH:13][C:12]=3[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O[CH3:28])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:28][N:13]1[C:14](=[O:16])[C:15]2=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[O:9][C:10](=[O:23])[C:11]2=[C:12]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 178517439HCID 178517439, compound

Product 1

HCID 12192481HCID 12192481, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of furopyrrole 6 (1.5 g, 4.08 mmol), methyl tosylate (1.14 g, 6.12 mmol), potassium carbonate (1.13 g, 8.16 mmol) and dimethylformamide 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 7 as a red solid (0.831 g, 53%), m.p. 215-216° C. δH (CDCl3) 8.19 and 7.61 (each 2H, AA′BB′, p-C6H4Br), 7.78-7.73 (2H, m, o-Ph), 7.54-7.50 (3H, m, m/p-Ph) and 3.38 (3H, s, NCH3). λmax (abs) (DCM)/nm 454 (ε 15,878)

Workup

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

Sources & evidence

ORD record
ord-73be27eb429d464eb4ebe623918e1b32
Source dataset
uspto-grants-2008_10
Patent number
US07442804B2

Reaction notes

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