Lithium iodide → HCID 67227816, compound

HRID 624333Notes

Reaction equation

HRID 624333 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-eba9709b7818455ea8b21756e3559e17
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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