Methanol → Methyl 2-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetate

HRID 230257Notes

Reaction equation

HRID 230257 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19]([OH:21])=[O:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.O=S(Cl)Cl.[CH3:26]O>>[CH3:26][O:20][C:19](=[O:21])[CH2:18][C:8]1[N:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 114259872-(6-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridin-3-yl)acetic acid

Product 1

HCID 9839075Methyl 2-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetateYield 80%

Procedure

To a magnetically stirred solution of (6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid 1a (5.0 g, 17.85 mmol) in methanol (MeOH) (25 mL) at 0° C. under Ar atmosphere was slowly added SOCl2 (2.60 mL, 35.7 mmol). The reaction mixture was stirred for 2 h and then concentrated in vacuo. Aqueous 10% Na2CO3 solution (100 mL) was added, and the aqueous phase was extracted with EtOAc (2×200 mL). The combined organic layers were washed with aqueous NaHCO3 solution, dried (MgSO4), and concentrated in vacuo to the provide the title compound (4.2 g, 80%) as yellow solids. 1H NMR (400 MHz, CDCl3) δ 2.37 (s, 3H), 2.40 (s, 3H), 3.76 (s, 3H), 4.03 (s, 2H), 7.07 (dd, J=1.7, 9.1 Hz, 1H), 7.28 (d, J=8.3 Hz, 2H), 7.55 (d, J=9.1 Hz, 1H), 7.70 (dd, J=1.8, 6.3 Hz, 2H), 7.85 (s, 1H). 13C-NMR (100 MHz, CDCl3) δ 18.7, 21.5, 30.8, 52.7, 112.4, 117.0, 121.5, 122.2, 127.8, 128.5, 129.6, 131.6, 137.7, 144.2, 144.6, 170.3.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. additionAqueous 10% Na2CO3 solution (100 mL) was added
  4. extractionthe aqueous phase was extracted with EtOAc (2×200 mL)
  5. washThe combined organic layers were washed with aqueous NaHCO3 solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo to the

Sources & evidence

ORD record
ord-9f875393226a4962b45227a580ee1125
Source dataset
uspto-grants-2009_07
Patent number
US07566725B2

Reaction notes

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