Lithium iodide → HCID 90386936, compound

HRID 2170212Notes

Reaction equation

HRID 2170212 reaction equation
C[O:2][C:3]1[C:8]2=[C:9]([CH3:33])[N:10]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:7]2[CH:6]=[C:5]([CH2:34][O:35][CH3:36])[N:4]=1.[I-].[Li+]>N1C=CC=CC=1>[CH3:36][O:35][CH2:34][C:5]1[NH:4][C:3](=[O:2])[C:8]2=[C:9]([CH3:33])[N:10]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:7]2[CH:6]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 90386969HCID 90386969, compound

Product 1

HCID 90386936HCID 90386936, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of Example 44c (0.0816 g, 0.162 mmol) and lithium iodide (0.65 g, 4.85 mmol) in pyridine (1 mL) was heated at 160° C. for 1 hour in a Biotage microwave reactor. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 20-80% ethyl acetate in heptanes) to provide 0.034 g (43%) of the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 20-80% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-12ff9cec0fc7466b98e901b5bcda43fe
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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