Water → HCID 118195069, compound

HRID 1048728Notes

Reaction equation

HRID 1048728 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][S:21][CH2:22][C:23](OCC)=[O:24])[CH:6]=[CH:7][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[F:28][C:2]([F:1])([F:29])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][S:21][CH2:22][CH2:23][OH:24])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 73052291HCID 73052291, compound

Product 1

HCID 118195069HCID 118195069, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under an argon atmosphere, 200 mg (0.446 mmol) of ethyl 2-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio)-acetate were dissolved in 4 ml of tetrahydrofurane and 33.9 mg (0.892 mmol) of LiAlH4 were added. The solution was heated to 50° C. for 1 h. 0.030 ml of water were slowly added, followed by the addition of 0.030 ml of 6N sodium hydroxide and then with 0.1 ml of water. After 30 min of stirring, the precipitate was filtered, and washed with ethyl acetate. The collected organic phases were washed with brine and then dried on Na2SO4 which was then removed by filtration and the obtained filtrate was concentrated in vacuo. The obtained solid was triturated in ethyl acetate, filtered and then washed with ethyl acetate. 50 mg (yield=28%) of 2-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)-methylthio) ethanol were obtained as a white solid. LC-MS: m/z=407 (MH+) UV purity at 254 nm=89%. 1H NMR (300 MHz, DMSO) δ 8.30 (d, 1H), 8.12 (s, 1H), 7.99 (m, 1H), 7.75 (m, 2H), 7.03 (m, 1H), 6.88 (d, 1H), 4.84 (t, 1H), 3.96 (s, 5H), 3.60 (m, 2H), 2.67 (t, 2H).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with ethyl acetate
  3. washThe collected organic phases were washed with brine
  4. customdried on Na2SO4 which
  5. customwas then removed by filtration
  6. concentrationthe obtained filtrate was concentrated in vacuo
  7. customThe obtained solid was triturated in ethyl acetate
  8. filtrationfiltered
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-8c4e382d7d1443ab9a35e11492e3cc5f
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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