Cesium carbonate → HCID 69939744, compound

HRID 714660Notes

Reaction equation

HRID 714660 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([CH2:38]Br)[CH:29]=1>C(#N)C>[Br:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([CH2:38][N:11]2[C:10](=[O:13])[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:18])([F:19])[F:17])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:12]2)[CH:29]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateHCID 584601185-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 69939744HCID 69939744, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

450 mg (1.30 mmol) of the compound from Example 4A and 715 mg (2.19 mmol) of cesium carbonate were suspended in 6 ml of acetonitrile, and 708 mg (1.61 mmol) of methyl 4-bromo-2-(bromomethyl)benzoate were added. The mixture was stirred under reflux for 20 h. The precipitated solid was filtered off and the filtrate was concentrated under reduced pressure to a volume of about 1.5 ml. After addition of 1 ml of 1 N hydrochloric acid, the mixture was directly purified chromatographically [Method 19]. This gave 545 mg (64% of theory) of the target compound in a purity of 92%.

Workup

  1. temperatureunder reflux for 20 h
  2. filtrationThe precipitated solid was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure to a volume of about 1.5 ml
  4. additionAfter addition of 1 ml of 1 N hydrochloric acid
  5. customthe mixture was directly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-95cc1da75d7341809dda5c707f839e7c
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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