HCID 58730939, compound → HCID 58730947, compound

HRID 1994200Notes

Reaction equation

HRID 1994200 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:4]=[C:5]2[CH2:11][CH2:10][NH:9][C:6]2=[N:7][CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 1

HCID 58730939HCID 58730939, compound

Product 1

HCID 58730947HCID 58730947, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the azaindoline 21 (20 mg, 0.10 mmol) in CH2Cl2 (2 mL) was added oven activated MnO2 (9 mg, 0.10 mmol) in one portion. After 18 h the mixture was filtered through a silica pad. The pad was washed with AcOEt and the combined organic solutions evaporated to afford the azaindole 22 (17 mg, 86%). 1H NMR (400 MHz; CDCl3) δ 0.35 (s, 9H), 6.50 (d, J=3.5 Hz, 1H), 7.35 (d, J=3.5 Hz, 1H), 8.10 (d, J=1.5 Hz, 1H), 8.40 (d, J=1.5 Hz, 1H), 10.62 (br s, NH).

Workup

  1. filtrationAfter 18 h the mixture was filtered through a silica pad
  2. washThe pad was washed with AcOEt
  3. customthe combined organic solutions evaporated

Sources & evidence

ORD record
ord-b2fc320c2f704cbcb81691945546d43b
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

Loading…