Potassium Iodide → HCID 86659834, compound

HRID 2039679Notes

Reaction equation

HRID 2039679 reaction equation
C([N:7]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](CO)N=1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])CCCCC.[CH:23]([N:26](CC)[CH:27]([CH3:29])[CH3:28])([CH3:25])[CH3:24].CS(Cl)(=O)=O.[OH:37][N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48].[C:49](=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[O:43]=[C:42]1[C:41]2[C:40](=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:39](=[O:48])[N:38]1[O:37][CH2:29][C:27]1[N:26]=[C:23]([CH2:24][CH2:17][CH2:18][CH2:19][CH2:20][CH2:15][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH:25]=[CH:49][CH:28]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 10665N-Hydroxyphthalimide2×HCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67425832HCID 67425832, compound

Product 1

HCID 86659834HCID 86659834, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl hexyl[6-(hydroxymethyl)pyridin-2-yl]carbamate (2.52 g, 8.18 mmol) in acetonitrile (50 mL) was added N,N-diisopropylethylamine (1.59 g, 12.2 mmol). The solution was cooled to 0° C., then methanesulfonyl chloride (1.12 g, 9.81 mmol) was slowly added. After stirring at room temperature for 6 h, N-hydroxyphthalimide (1.46 g, 8.96 mmol), cesium carbonate (5.58 g, 17.1 mmol) and potassium iodide (135 mg, 0.81 mmol) were sequentially added, followed by acetonitrile (10 mL). The heterogenous mixture was stirred at room temperature for 20 h, then N-hydroxyphthalimide (0.33 g, 2.0 mmol) was added and the mixture was stirred at 50° C. for 7 h. The cooled reaction mixture was filtered and the filtrate was concentrated in vacuo. The oily residue was dissolved in ethyl acetate (200 mL), washed with water (100 mL), the organic layer was dried (MgSO4) and concentrated in vacuo. Purification on silica gel afforded tert-butyl (6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)hexylcarbamate as a yellow oil [2.107 g, yield 57%; HPLC/MS: m/z=454 (M+H); log P(HCOOH)=5.48].

Workup

  1. stirringThe heterogenous mixture was stirred at room temperature for 20 h
  2. stirringthe mixture was stirred at 50° C. for 7 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe oily residue was dissolved in ethyl acetate (200 mL)
  7. washwashed with water (100 mL)
  8. dry with materialthe organic layer was dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification on silica gel

Sources & evidence

ORD record
ord-a7404ef82d9741c899f5799c0a371d95
Source dataset
uspto-grants-2013_11
Patent number
US08580799B2

Reaction notes

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