Isopropanol → 4-Isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile
Reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].Cl[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[N:14]=2)[N:9]=[CH:8][C:7]=1[C:17]#[N:18]>C1COCC1>[CH:1]([O:4][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[N:14]=2)[N:9]=[CH:8][C:7]=1[C:17]#[N:18])([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
To a 50 mL flask placed with KH (30%, 685 mg, 6.0 mmol, pre-washed with nHex) was added a solution of anhydrous isopropanol (0.76 mL, 10.0 mmol) in anhydrous THF (5 mL) at room temperature under argon. The reaction mixture was cooled to −20° C. 4-chloro-6-methyl-[1,5]naphthyridine-3-carbonitrile (407.0 mg, 2.0 mmol) in THF (8 mL) was added dropwise and the reaction mixture was stirred at −20° C. to r.t for 30 min. The reaction mixture was quenched with sat.NH4Cl and extracted with AcOEt (100 mL×3). The combined organic layers was dried over Na2SO4 and concentrated to give the crude product which was purified by flash column (AcOEt/Hex=1/3˜3/2) to give 4-Isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile as white solid (240.0, 52.8%) which was used in the next step without further purification.
Workup
- washTo a 50 mL flask placed with KH (30%, 685 mg, 6.0 mmol, pre-washed with nHex)
- customThe reaction mixture was quenched
- extractionNH4Cl and extracted with AcOEt (100 mL×3)
- dry with materialThe combined organic layers was dried over Na2SO4
- concentrationconcentrated
- customto give the crude product which
- customwas purified by flash column (AcOEt/Hex=1/3˜3/2)
Sources & evidence
- ORD record
- ord-8ce567da35ee44d6928772475db98fe0
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07304074B2
Reaction notes
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