Water → 1-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-ol

HRID 1295876Notes

Reaction equation

HRID 1295876 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:19]=[O:20])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]([Mg]Br)#[CH:22].O.CCOCC>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:19]([OH:20])[C:21]#[CH:22])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 878860048-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridine-3-carbaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 179681531-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.) solution of 8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridine-3-carbaldehyde (1.06 g, 3.70 mmol) in tetrahydrofuran (20 mL) was added ethynyl magnesium bromide (18.53 mL, 0.5 M in tetrahydrofuran, 9.26 mmol). After 15 minutes, the resulting mixture was allowed to warm to room temperature and stirred an additional 30 minutes. Water was added and then ether. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:1 hexanes-ethyl acetate to 100% ethyl acetate) provided 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-ol (910 mg, 79%) as a white solid. 1H NMR (CDCl3): δ 8.61 (d, 1 H), 7.33–7.26 (m, 2 H), 7.16–7.11 (m, 2 H), 6.88 (m, 1 H), 6.79 (m, 1 H), 6.14 (m, 1 H), 3.85 (s, 3 H), 3.27 (broad, 1 H), 2.64 (d, 1 H); 13C NMR (CDCl3): δ 159.64, 144.46, 134.12, 129.56, 124.99, 124.51, 123.03, 121.37, 119.43, 114.54, 114.13, 111.81, 111.27, 79.96, 75.03, 55.88, 55.38; MS m/z 313 (M+1); Anal. Calcd. for C17H13ClN2O2: C, 65.29; H, 4.19; N, 8.96. Found: C, 65.23; H, 4.34; N, 8.81.

Workup

  1. washThe organic layer was washed with brine
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialthe combined organics were dried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1dd4786630b5494b82ea2173b3851bbb
Source dataset
uspto-grants-2007_07
Patent number
US07244740B2

Reaction notes

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