Imidazole → HCID 123278338, compound

HRID 2202690Notes

Reaction equation

HRID 2202690 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([OH:17])[CH2:13][N+:14]([O-:16])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C=CN=C1.[CH2:23]([Si:25](Cl)([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([O:17][Si:25]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:23][CH3:24])[CH2:13][N+:14]([O-:16])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 118342895HCID 118342895, compound

Product 1

HCID 123278338HCID 123278338, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a brown clear solution of 1-(3-chloroquinolin-4-yl)-2-nitroethanol (A275-4) (0.423 g, 1.68 mmol) in DMF (4.19 mL) at room temperature was added imidazole (0.342 g, 5.03 mmol) and triethylsilyl chloride (0.341 mL, 2.01 mmol). The mixture was stirred at room temperature. After 2 h, the mixture was quenched with water (50 mL) and extracted with EtOAc (2×50 mL). The organic extract washed with 1 M LiCl (1×50 mL) and brine (1×50 mL), and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow syrup. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a REDISEP pre-packed silica gel column (40 g), eluting with a gradient of 0% to 10% EtOAc in hexane, and dried under high vacuum to give 3-chloro-4-(2-nitro-1-((triethylsilyl)oxy)ethyl)quinoline (A275-5). 1H NMR (400 MHz, DMSO-d6) δ 8.95 (1H, s), 8.67 (1H, d, J=7.4 Hz), 8.10 (1H, dd, J=8.4, 0.8 Hz), 7.84 (1H, td, J=7.6, 1.4 Hz), 7.71-7.79 (1H, m), 6.38 (1H, dd, J=9.8, 2.5 Hz), 5.14-5.23 (1H, m), 5.03-5.11 (1H, m), 0.65-0.74 (9H, m), 0.32-0.51 (6H, m); LCMS (ESI) m/z 367.1 (M+H)+.

Workup

  1. customthe mixture was quenched with water (50 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. extractionThe organic extract
  4. washwashed with 1 M LiCl (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material as a yellow syrup
  9. customThe crude material was absorbed onto a plug of silica gel
  10. custompurified by chromatography through a REDISEP pre-packed silica gel column (40 g)
  11. washeluting with a gradient of 0% to 10% EtOAc in hexane
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-833cb71785ee46918d805c1af95b6191
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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