Dichloromethane → HCID 59170308, compound

HRID 1445940Notes

Reaction equation

HRID 1445940 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][NH:13][C:12](=[O:17])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:20]Cl.F[B-](F)(F)F.C[O+](C)C>>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:17][CH3:20])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 591703201-Benzyl-2-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 59170308HCID 59170308, compoundYield 35%

Procedure

To a mixture of 1-benzyl-2-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (1) (3.48 g, 16.62 mmole) in dichloromethane (160 mL) trimethyloxonium tetrafluoroborate (4.52 g, 29.24 mmole) was added. The mixture was stirred at room temperature for 18 h. Additional trimethyloxonium tetrafluoroborate (2.25 g, 14.55 mmole) was added and stirred for 18 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (20:1 CH2Cl2:MeOH) to afford intermediate (2) Yield: 1.31 g, 35%.

Workup

  1. additionwas added
  2. stirringstirred for 18 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (20:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-fd89634c8c6b4202afae1d74b0e995b2
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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