HCID 57893515, compound → HCID 57893557, compound

HRID 1821856Notes

Reaction equation

HRID 1821856 reaction equation
[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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>[O-2].[O-2].[Mn+4]>[CH2:26]([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]([C:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 57893515HCID 57893515, compound

Product 1

HCID 57893557HCID 57893557, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

[5-(Dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol (Example 54) was oxidized using manganese dioxide to provide [5-(dibenzylamino)-1 h-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone following the procedure described for Example 139 using methylene chloride as a solvent. Trituration of the crude material with Et2O provided [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone (220 mg, 44%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ4.77 (4H, s), 6.69 (1H, s), 6.82 (1H, s), 7.19-7.27 (10H, m), 7.53-7.65 (3H, m), 7.92-7.95 (2H, m), 8.57 (1H, s); ESI MS m/z 418 [C28H23N3O+H]+; HPLC (Method A) >99% (AUC), tR=20.9 min.

Sources & evidence

ORD record
ord-81a8f269e78541938a93c410bb4b4569
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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