HCID 57893465, compound → HCID 57893510, compound

HRID 1821838Notes

Reaction equation

HRID 1821838 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:12])[NH:8][C:7]=12>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:12])[NH:8][C:7]=12

Participants

4

Reactant 1

HCID 57893465HCID 57893465, compound

Product 1

HCID 57893510HCID 57893510, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (Example 26) (0.83 g, 3.2 mmol) and MnO2 (3.35 g, 38.5 mmol) in methylene chloride (64 mL) was stirred under a nitrogen atmosphere at room temperature overnight (20 h). The crude reaction mixture was filtered through diatomaceous earth and rinsed with methylene chloride. Concentration afforded (7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanone (0.68 g, 82%) as an off-white solid: mp 152-153° C.; 1H NMR (300 MHz, CDCl3) δ7.18 (1H, d, J=2.1 Hz), 7.55-7.71 (4H, m), 7.99-8.05 (2H, m), 8.11 (1H, d, J=5.7 Hz), 9.55 (1H, br s); ESI MS m/z 257 [C14H9ClN2O+H]+; HPLC (Method A) >99% (AUC), tR=25.0 min.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through diatomaceous earth
  3. washrinsed with methylene chloride
  4. concentrationConcentration

Sources & evidence

ORD record
ord-5d0ed49ca70c4079a579bc0f8414e311
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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