HCID 57893488, compound → HCID 57893525, compound

HRID 1821857Notes

Reaction equation

HRID 1821857 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]([OH:20])[CH3:19])[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]>[CH2:21]([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](=[O:20])[CH3:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 1

HCID 57893488HCID 57893488, compound

Product 1

HCID 57893525HCID 57893525, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

1-[5-(Dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]ethanol (Example 53) was oxidized using manganese dioxide to provide 1-[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]ethanone following the procedure described for Example 139 using tetrahydrofuran as a solvent. Purification by Biotage chromatography provided 1-[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]ethanone (200 mg, 40%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ2.54 (3H, s), 4.76 (4H, s), 6.67 (1H, s), 6.97 (1H, s), 7.12-7.30 (10H, m), 8.50 (1H, s); ESI m/z 356 [C23H21N30+H]+; HPLC (Method A) >99% (AUC), tR=18.8 min.

Sources & evidence

ORD record
ord-433fa741645c48dc91ec7c9a37787153
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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