N-Iodosuccinimide → HCID 86724446, compound

HRID 870957Notes

Reaction equation

HRID 870957 reaction equation
[CH3:1][CH:2]([CH3:30])[CH2:3][C@H:4]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:20]3[C:15](=[CH:16][N:17]=[CH:18][CH:19]=3)[CH:14]([CH3:21])[O:13][C:11]=2[CH:12]=1.C1C(=O)N([I:38])C(=O)C1>C(#N)C>[I:38][C:8]1[C:7]([O:6][CH2:5][C@@H:4]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:3][CH:2]([CH3:30])[CH3:1])=[CH:12][C:11]2[O:13][CH:14]([CH3:21])[C:15]3[C:20]([C:10]=2[CH:9]=1)=[CH:19][CH:18]=[N:17][CH:16]=3

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86724447HCID 86724447, compound

Product 1

HCID 86724446HCID 86724446, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl ((2S)-4-methyl-1-((5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)carbamate (200 mg, 0.485 mmol) in acetonitrile (4 mL) was added NIS (654 mg, 2.91 mmol) and the mixture refluxed at 80° C. for 12 h. The volatiles were removed under reduced pressure. The residue was dissolved in water (10 mL) and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (15 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (pet ether: ethyl acetate) to afford tert-butyl ((2S)-1-((9-iodo-5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (150 mg, 0.237 mmol, 49% yield) as a dark brown oil. LCMS (ESI) m/e 539.0 [(M+H)+, calcd for C24H321N2O4539.1]; LC/MS retention time (method D): tR=1.84 min.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  4. washThe combined organic layers were washed with brine (15 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography (pet ether: ethyl acetate)

Sources & evidence

ORD record
ord-37f0b8a79cc54790be26a15793957e72
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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