Sodium hydride → HCID 59432339, compound

HRID 507023Notes

Reaction equation

HRID 507023 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:27]=[CH:26][C:7]2[N:8]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:10][CH2:11][CH:12]([NH:13][C:14]3[S:18][N:17]=[C:16]([CH3:19])[CH:15]=3)[C:6]=2[CH:5]=1.[F:28][C:29]([F:43])([F:42])[C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:33]Br>O1CCCC1.C(OCC)(=O)C>[F:28][C:29]([F:42])([F:43])[C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:37]=1)[CH2:33][N:13]([C:14]1[S:18][N:17]=[C:16]([CH3:19])[CH:15]=1)[CH:12]1[CH2:11][CH2:10][CH2:9][N:8]([C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])[C:7]2[CH:26]=[CH:27][C:4]([Br:3])=[CH:5][C:6]1=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 59432488HCID 59432488, compound

Product 1

HCID 59432339HCID 59432339, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add sodium hydride to a stirring solution of isopropyl 7-bromo-5-(3-methylisothiazol-5-ylamino)-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate in anhydrous tetrahydrofuran at room temperature under nitrogen. After the appropriate stirring time, treat the mixture with 3,5-bis(trifluoromethyl)benzyl bromide and continue stirring for an appropriate time. Dilute the mixture with ethyl acetate, wash with water and brine and dry over sodium sulfate. Remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel to provide the title compound.

Workup

  1. washwash with water and brine
  2. dry with materialdry over sodium sulfate
  3. customRemove the solvents under reduced pressure
  4. custompurify the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-90c72dbcea0844eb88207ca3a6e1bc98
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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