HCID 57893533, compound → HCID 57893538, compound

HRID 1821908Notes

Reaction equation

HRID 1821908 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH2:18][OH:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 57893533HCID 57893533, compound

Product 1

HCID 57893538HCID 57893538, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (Example 48) (9.74 g, 28.4 mmol) and manganese dioxide (24.6 g, 283.6 mmol) in methylene chloride (584 mL) was stirred at room temperature under a nitrogen atmosphere overnight (15 h). The reaction mixture was filtered through diatomaceous earth to remove the manganese dioxide. Concentration of the filtrate provided the crude material as a dark solid. The crude material was purified by trituration with toluene to give 5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (6.36 g, 65%) as an orange solid: 1H NMR (300 MHz, CDCl3) δ4.84 (4H, s), 6.60 (1H, s), 6.95 (1H, s), 7.21-7.33 (10H, m), 8.63 (1H, s), 9.75 (1H, br s), 9.86 (1H, s).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customto remove the manganese dioxide
  3. customConcentration of the filtrate provided the crude material as a dark solid
  4. customThe crude material was purified by trituration with toluene

Sources & evidence

ORD record
ord-e6cdb975d5b14e26a63818d978091449
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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