HCID 57893459, compound → HCID 57893472, compound

HRID 1821870Notes

Reaction equation

HRID 1821870 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]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:5]2=[CH:6][N:7]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]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:5]2=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 57893459HCID 57893459, compound

Product 1

HCID 57893472HCID 57893472, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(5-Chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (Example 140) (105 mg, 0.41 mmol) was dissolved in methylene chloride (10 mL). Manganese dioxide (358 mg, 4.1 mmol) was added and the reaction mixture was stirred for 60 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with methylene chloride. The filtered was concentrated to give a pink solid. Recrystallization from methylene chloride gave (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanone (73 mg, 70%) as a white solid: mp 194-197° C.; 1H NMR (300 MHz, CDCl3) δ7.10 (1H, s), 7.51-7.75 (4H, m), 8.01 (2H, m), 8.79 (1H, s), 9.57 (1H, br s); ESI MS m/z 257 [C14H9ClN2O+H]+; HPLC (Method A) >99% (AUC), tR=21.5 min.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed several times with methylene chloride
  3. concentrationThe filtered was concentrated
  4. customto give a pink solid
  5. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-b2831fb3ded049f399a0d20e6ea381d0
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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