Diisopropylethylamine → (3-(2-Tert-butylphenoxy)azetidin-1-yl)(imidazo[1,2-a]pyridin-2-yl)methanone

HRID 2041985Notes

Reaction equation

HRID 2041985 reaction equation
[N:1]1[C:2]([C:10]([O-:12])=O)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[Na+].[C:14]([C:18]1[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=1[O:20][CH:21]1[CH2:24][NH:23][CH2:22]1)([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:14]([C:18]1[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=1[O:20][CH:21]1[CH2:22][N:23]([C:10]([C:2]2[N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][N:4]3[CH:3]=2)=[O:12])[CH2:24]1)([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24229477Sodium imidazo[1,2-a]pyridine-2-carboxylateHCID 534095303-(2-Tert-butylphenoxy)azetidine

Product 1

HCID 59577285(3-(2-Tert-butylphenoxy)azetidin-1-yl)(imidazo[1,2-a]pyridin-2-yl)methanoneYield 97.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of sodium imidazo[1,2-a]pyridine-2-carboxylate (0.19 g, 1.0 mmol), 3-(2-tert-butylphenoxy)azetidine (0.21 g, 0.53 mmol) and DIPEA (0.39 g, 3.0 mmol) in DMF (5.0 mL) was added HBTU (0.76 g, 2.0 mmol) at room temperature. After 1 h the reaction mixture was diluted with ethyl acetate (50 mL) and washed with a 10% K2CO3 solution (3×20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, ethyl acetate to 95:5 methanol/ethyl acetate) to provide (3-(2-tert-butylphenoxy)azetidin-1-yl)(imidazo[1,2-a]pyridin-2-yl)methanone (0.18 g, 51%) as a white solid.

Workup

  1. washwashed with a 10% K2CO3 solution (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, ethyl acetate to 95:5 methanol/ethyl acetate)

Sources & evidence

ORD record
ord-b499ebed751241d48f953bf8adddb471
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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