[7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol → [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone

HRID 1821850Notes

Reaction equation

HRID 1821850 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[N:10]=[CH:11][CH:12]=[C:13]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:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[CH2:26]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]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:14]=12)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 57893455[7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol

Product 1

HCID 57893469[7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol (Example 46) (1.13 g, 2.69 mmol) and MnO2 (2.35 g, 27.0 mmol) in methylene chloride (75 mL) was stirred under a nitrogen atmosphere at room temperature overnight (17 h). The crude reaction mixture was filtered through diatomaceous earth, rinsing with methylene chloride. The filtrate was concentrated to give a dark oil. Purification by Biotage chromatography (10-30% ethyl acetate in hexanes) provided [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone as a yellow solid: mp 122-124° C.; 1H NMR (300 MHz, CD3OD) δ4.76 (4H, s), 5.49 (1H, s), 6.25 (1H, s), 7.11 (1H, s) 7.15-7.30 (10H, m), 7.56-7.72 (4H, m), 7.94-7.97 (2H, m); ESI MS m/z 418 [C28H23N3O+H]+; HPLC (Method A) >99% (AUC), tR=20.2 min.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through diatomaceous earth
  3. washrinsing with methylene chloride
  4. concentrationThe filtrate was concentrated
  5. customto give a dark oil
  6. customPurification by Biotage chromatography (10-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9aa89d977e204de1b075e6cea3d91e74
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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