HCID 86747698, compound → HCID 19091489, compound

HRID 487911Notes

Reaction equation

HRID 487911 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:7]([C:11](=[O:13])[CH3:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:51][Mg]Br>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:7]([C:11]([CH3:51])([CH3:12])[OH:13])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 86747698HCID 86747698, compoundHCID 178418573HCID 178418573, compound3×

Product 1

HCID 19091489HCID 19091489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.444 g of the product of Example 4 in 10 ml of tetrahydrofuran, cooled to 0° C. is slowly added 0.656 ml of 3.0 M methylmagnesium bromide. The cooling bath is removed after 0.5 hour and reaction mixture allowed to warm to room temperature and stir for 2 hours. An additional 1.2 ml of 3.0 M methyl magnesium bromide is added and the reaction mixture stirred at room temperature for 0.5 hour. An additional 1.0 ml of 3.0 M methyl magnesium bromide is added an the reaction mixture stirred at room temperature for 0.5 hour. The reaction mixture is quenched with saturated ammonium chloride and diluted with water, followed by extraction with ethyl acetate. The organic layer is dried with MgSO4, filtered and concentrated to give a crude solid which is purified by column chromatography on silica gel with 1:2 ethyl acetate-hexane to give 0.706 g of the desired product as a solid. FAB MASS SPEC 693(M+ H).

Workup

  1. customThe cooling bath is removed after 0.5 hour
  2. customreaction mixture
  3. stirringthe reaction mixture stirred at room temperature for 0.5 hour
  4. stirringstirred at room temperature for 0.5 hour
  5. customThe reaction mixture is quenched with saturated ammonium chloride
  6. additiondiluted with water
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe organic layer is dried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a crude solid which
  12. customis purified by column chromatography on silica gel with 1:2 ethyl acetate-hexane

Sources & evidence

ORD record
ord-cc9dcd80b84340f8a0e4c9de4ba2bc7d
Source dataset
uspto-grants-1994_03
Patent number
US05298517

Reaction notes

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