Lithium iodide → HCID 67227816, compound

HRID 1043064Notes

Reaction equation

HRID 1043064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[C:23]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=4)[CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[Li+].[I-]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[C:23]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=4)[CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 67226652HCID 67226652, compound

Product 1

HCID 67227816HCID 67227816, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of EXAMPLE 22A (0.081 g) in pyridine (2 mL) in a 10 mL microwave vial equipped with a magnetic stir bar was treated with LiI (0.402 g), flushed with nitrogen and heated in a CEM microwave reactor at 120° C. for 30 minutes. The mixture was concentrated, acidified with 1N HCl, extracted with ethyl acetate and dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel, eluting with a gradient of 0-10% methanol in dichloromethane.

Workup

  1. customflushed with nitrogen
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography on silica gel
  8. washeluting with a gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-8356728640e34257b0800169555df4dd
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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