Methyl morpholine oxide → 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

HRID 588089Notes

Reaction equation

HRID 588089 reaction equation
Br[CH2:2][C:3]1[C:8]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:6]=[C:5]([Cl:33])[N:4]=1.C[N+]1([O-])CC[O:38]CC1>C1COCC1>[Cl:33][C:5]1[N:4]=[C:3]([CH:2]=[O:38])[C:8]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 1182717894-(bromomethyl)-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1182719996-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Bromomethyl)-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (165 mg, 0.318 mmol) was dissolved in THF (4 mL), charged with NMO (112 mg, 0.954 mmol), and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (10-50% EtOAc/hexanes) to give 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde. 1H NMR (500 MHz, CDCl3) δ 10.41 (s, 1H), 7.31 (m, 10H), 7.20 (m, 5H), 6.08 (s, 1H), 4.00 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a42e0d1388e74eb39edcfb7c42987796
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…