Sulfuric Acid → HCID 90031842, compound

HRID 1048714Notes

Reaction equation

HRID 1048714 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]#[C:14][C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][C:16]=2[C:24](OCC)=[O:25])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(=O)(=O)(O)O>O1CCCC1.O>[C:7]1([C:13]#[C:14][C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][C:16]=2[CH2:24][OH:25])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 101451949HCID 101451949, compound

Product 1

HCID 90031842HCID 90031842, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

In a flask placed under an argon flow, 0.078 g (1.984 mmol) of LAH were dissolved in 1.4 ml of tetrahydrofurane and then with vigorous magnetic stirring, a solution of 0.3 g (0.992 mmol) of ethyl 3-(phenylethynyl)imidazo[1,2-a]pyridine-2-carboxylate in 3.3 ml of tetrahydrofurane was added drop wise. The mixture was stirred at r.t. for 15 min and then 0.2 ml of water were added with caution, followed by a solution of 0.2 ml of sulfuric acid in 1.5 ml of water. After separation, the organic phase was washed with 50 ml of water. The aqueous phase was extracted with 3×50 ml of ethyl acetate and then the combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution and then dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate gradient, from 40% to 30% of heptane, v/v). 0.076 g (yield=30%) of (3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methanol were obtained as a pale yellow solid. LC-MS: m/z=249 (MH+); UV purity at 254 nm=97%. 1H NMR (300 MHz, DMSO) δ 8.59 (dt, J=6.7, 1.1 Hz, 1H), 7.77-7.56 (m, 3H), 7.56-7.32 (m, 4H), 7.11 (td, J=6.8, 1.1 Hz, 1H), 5.33 (t, J=5.9 Hz, 1H), 4.67 (d, J=5.9 Hz, 2H).

Workup

  1. customIn a flask placed under an argon
  2. customAfter separation
  3. washthe organic phase was washed with 50 ml of water
  4. extractionThe aqueous phase was extracted with 3×50 ml of ethyl acetate
  5. washthe combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution
  6. customdried on Na2SO4 which
  7. customwas then removed by filtration
  8. concentrationThe obtained filtrate was concentrated in vacuo
  9. customThe crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate gradient, from 40% to 30% of heptane, v/v)

Sources & evidence

ORD record
ord-5b71d70682a04547b3eebf292db02873
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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