Trimethylamine oxide → HCID 59529740, compound

HRID 1952329Notes

Reaction equation

HRID 1952329 reaction equation
C[N+]([O-:5])(C)C.Br[CH2:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:9]=1>ClCCl>[CH:7]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:9]=1)=[O:5]

Participants

4

Reactant 2

HCID 1145Trimethylamine oxideHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 59529740HCID 59529740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Solid trimethylamine N-oxide (241 mg; 3.20 mmol) was added to a solution of tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (1-1; 400 mg; 1.281 mmol) in dichloromethane, and the resulting reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane, washed with brine (2×), dried over MgSO4, and evaporated to give the title compound I-A as a white solid. MS M+1=148.1. 1H NMR (CDCl3): 1.75 (s, 9H), 7.42 (m, 1H), 8.64 (d, 1H), 8.80 (d, 1H), 10.28 (s, 1H).

Workup

  1. customthe resulting reaction mixture
  2. washwashed with brine (2×)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-2cbc8029473f4e53b044db1a84394934
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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