Sulfuric Acid → HCID 73051806, compound

HRID 1048690Notes

Reaction equation

HRID 1048690 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][C:11]=2[CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:30](O)([CH3:32])[CH3:31]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][C:11]=2[CH2:19][O:20][CH2:21][C:22]([O:24][CH:30]([CH3:32])[CH3:31])=[O:23])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 73051327HCID 73051327, compound

Product 1

HCID 73051806HCID 73051806, compoundYield 91%

Conditions

Temperature
60 °C

Procedure

0.155 g (0.478 mmol) of 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl) methoxy)acetic acid were solubilized with magnetic stirring in 5 ml of isopropanol and a drop of sulfuric acid was added. The mixture was stirred at 60° C. for 3 h. The reaction medium was washed with 2×10 ml of water, and then extracted with 2×30 ml of ethyl acetate. The combined organic phases were washed with 30 ml of a saturated NaCl aqueous solution, dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. 0.162 mg (yield=91%) of isopropyl 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)-methoxy)acetate were obtained as a brown oil. LC-MS: m/z=367 (MH+); UV purity at 254 nm=98%. 1H NMR (300 MHz, DMSO) δ 8.62 (d, J=6.8 Hz, 1H), 7.74 (dd, J=8.7, 5.5 Hz, 2H), 7.67 (d, J=9.0 Hz, 1H), 7.45 (d, J=7.0 Hz, 1H), 7.33 (t, J=8.9 Hz, 2H), 7.12 (t, J=6.5 Hz, 1H), 4.93 (dt, J=12.5, 6.3 Hz, 1H), 4.78 (s, 2H), 4.19 (s, 2H), 1.15 (d, J=6.3 Hz, 6H).

Workup

  1. washThe reaction medium was washed with 2×10 ml of water
  2. extractionextracted with 2×30 ml of ethyl acetate
  3. washThe combined organic phases were washed with 30 ml of a saturated NaCl aqueous solution
  4. customdried on Na2SO4 which
  5. customwas then removed by filtration
  6. concentrationThe obtained filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-96ab72f783164216bc6fcd2442b44860
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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