Isopropanol → 8-Isopropoxy-2-methyl-[1,5]naphthyridine

HRID 968739Notes

Reaction equation

[CH:1]([OH:4])([CH3:3])[CH3:2].Cl[C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2>C1COCC1>[CH:1]([O:4][C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

To a 100 mL flask placed with KH (30%, 2.7 g, 20.15 mmol, pre-washed with nHex) was added a solution of anhydrous isopropanol (2.04 g, 33.59 mmol) in anhydrous THF (15 mL) at room temperature under argon. The reaction mixture was cooled to −20° C. 8-chloro-2-methyl-[1,5]naphthyridine (1.20 g, 6.72 mmol) in THF (20 mL) was added dropwise and the reaction mixture was stirred at −20° C. to r.t for 2 hrs. The reaction mixture was poured into 20 mL ice-water 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 8-isopropoxy-2-methyl-[1,5]naphthyridine as white solid (0.34 g, 25%). HR-MS-EI (+) m/e calcd for C12H14N2O (M+) 202.1106. found 202.1107.

Workup

washTo a 100 mL flask placed with KH (30%, 2.7 g, 20.15 mmol, pre-washed with nHex)
extractionextracted 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-87ab8f14775b48d0903136148842c953
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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