HCID 67398160, compound → HCID 86641684, compound

HRID 2060676Notes

Reaction equation

HRID 2060676 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:16]=[N:17][C:18]([CH2:21][OH:22])=[CH:19][CH:20]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:16]=[N:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67398160HCID 67398160, compound

Product 1

HCID 86641684HCID 86641684, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [4-(6-hydroxymethyl-pyridin-3-yloxy)-phenyl]-carbamic acid t-butyl ester (0.25 g, 0.8 mmol) in DCM (3.0 ml) was treated with activated MnO2 (0.42 g, 4.8 mmol) and the suspension was stirred at RT for 2 h. The reaction suspension was filtered and the filtrate was concentrated in vacuo to provide [4-(6-formyl-pyridin-3-yloxy)-phenyl]-carbamic acid t-butyl ester (0.24 g, 95% yield). MS (ESI) m/z: 315.0 (M+H+).

Workup

  1. filtrationThe reaction suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa4df27d363e495ebc4977f4eef985bf
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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