N-Iodosuccinimide → HCID 66779473, compound

HRID 1470337Notes

Reaction equation

HRID 1470337 reaction equation
[I:1]N1C(=O)CCC1=O.[F-].[K+].[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([Si](C)(C)C)[O:20][C:13]=12>C(#N)C>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([I:1])[O:20][C:13]=12

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 522689Potassium FluorideHCID 594273397-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine

Product 1

HCID 66779473HCID 66779473, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

N-Iodo succinimide (110 g, 0.486 mol) and potassium fluoride (3.2 g, 0.053 mol) are added to a stirred solution of 7-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine (11 g, 0.0486 mol) in dry acetonitrile (65 ml) at RT. The reaction mixture is heated at 50° C. for 2 h under nitrogen, cooled to RT and evaporate under reduced pressure. The residue is dissolved in ethyl acetate (500 ml), washed with saturated sodium thiosulfate (100 ml×2), water (100 ml×2) and saturated brine (100 ml), dried over sodium sulphate and concentrated under reduced pressure to afford the title compound (10.5 g, 77.3%) as an off white solid. TLC: hexane/ethyl acetate: (8/2): Rf=0.60; LCMS (method D): 3.49 min (purity 97.7%), M+H+ 279.8; 1H NMR (DMSO-d6, 400 MHz) δ [ppm] 8.41-8.405 (1H, d, J=5.3 Hz), 7.545 (1H, s), 7.448-7.435 (1H, d, J=5.2 Hz).

Workup

  1. temperaturecooled to RT
  2. customevaporate under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate (500 ml)
  4. washwashed with saturated sodium thiosulfate (100 ml×2), water (100 ml×2) and saturated brine (100 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73f0992c3d4a4f73a01271d931ecba14
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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