Isopropylamine → (2-Isopropylamino-pyridin-4-yl)-methanol

HRID 45106Notes

Reaction equation

HRID 45106 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11]>O1CCOCC1.C(Cl)Cl>[CH:10]([NH:13][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 59394019(2-Isopropylamino-pyridin-4-yl)-methanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (2-bromo-pyridin-4-yl)-methanol (500 mg, 2.66 mmol), isopropylamine (0.45 mL, 5.32 mmol), NatOBu (790 mg, 7.98 mmol) and Pd(tBu3P)2 (136 mg, 0.26 mmol) in 1,4-dioxane (5 mL) is heated in a microwave reactor at 110° C. for 45 min. The reaction is diluted with DCM (50 mL) and washed with saturated aqueous NH4Cl. The organic layer is removed, dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound that is used without further purification. MS (ESI) m/z 167.1 (M+1).

Workup

  1. washwashed with saturated aqueous NH4Cl
  2. customThe organic layer is removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09b5d08649594c94ad5f404cc631c31f
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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