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

HRID 450253Notes

Reaction equation

HRID 450253 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-9acaf265c4754df6aa104ad0c6f91bae
Source dataset
uspto-grants-2013_07
Patent number
US08486954B2

Reaction notes

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