Sodium Hydroxide → HCID 68656890, compound

HRID 1626996Notes

Reaction equation

HRID 1626996 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:16]1[CH:17]=[CH:18][C:19]([C:22](OC)=[O:23])=[N:20][CH:21]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.C(OCC)C.O>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:14])([CH3:15])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:16]1[CH:17]=[CH:18][C:19]([CH2:22][OH:23])=[N:20][CH:21]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 70978550HCID 70978550, compound

Product 1

HCID 68656890HCID 68656890, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]pyridine-2-carboxylate (132 mg, 0.327 mmol) in THF (3 ml) was cooled to −78° C., followed by the dropwise addition of lithium aluminum hydride (0.360 ml, 1M THF solution, 0.360 mmol). After 1 hour, the mixture was treated with water (15 uL), 2N aqueous sodium hydroxide (15 uL) and water (45 uL). The mixture was warmed to room temperature, diluted with diethyl ether and treated with magnesium sulfate. After stirring for 30 minutes, the mixture was filtered through celite and concentrated in vacuo. The residue was purified via silica gel chromatography (methanol/dichloromethane gradient), providing the titled compound: LRMS m/z (M+H) 375.0 and 377.0 found, 375.1 and 377.1 required.

Workup

  1. filtrationthe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via silica gel chromatography (methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-fbeb6927eb1941cca46a5b62a2630b77
Source dataset
uspto-grants-2014_07
Patent number
US08785482B2

Reaction notes

Loading…