Cesium carbonate → HCID 59016003, compound

HRID 968861Notes

Reaction equation

HRID 968861 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]([CH2:26][CH2:27][CH3:28])[C:12](=[O:25])[N:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:36]([CH3:43])([CH3:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38]>CN(C=O)C>[CH2:40]([O:39][C:37](=[O:38])[C:36]([CH3:43])([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]([CH2:26][CH2:27][CH3:28])[C:12](=[O:25])[N:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:14]=2)=[CH:4][CH:3]=1)[CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 59016033HCID 59016033, compound

Product 1

HCID 59016003HCID 59016003, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 5-[2-(4-Hydroxyphenyl)ethyl]-4-propyl-2-(4-trifluoromethylphenyl)-2,4-dihydro-[1,2,4]triazol-3-one (0.10 g, 0.26 mmol) and cesium carbonate (0.16 g, 0.49 mmol) in anhydrous DMF (2.5 mL) was added ethyl 2-bromoisobutyrate (81.1 mg, 60.6 □L, 0.42 mmol). The reaction mixture was heated to 75° C. overnight. More ethyl 2-bromoisobutyrate (30.3 □L) was added and the mixture was stirred at 110° C. overnight and ambient temperature over the weekend. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic extracts were washed with 5% aqueous lithium chloride solution, water, brine, dried and evaporated. Chromatotron chromatography (gradient of ethyl acetate in hexanes) gave the pure compound (94 mg, 70.7%): 1HNMR (400 MHz, CDCl3) δ 8.14 (m, 2H), 7.65 (m, 2 H,), 7.10 (m, 2H), 6.80 (m, 2H), 4.23 (m, 2H), 3.53 (m, 2 H), 3.05 (m, 2H), 2.83 (m, 2H), 1.70 (m, 2H), 1.57 (s, 6 H), 1.26 (m, 6H); ESMS m/z (relative intensity) 506.1 (M+H+, 100).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with 5% aqueous lithium chloride solution, water, brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-b78f76521de4441f82efc7a030db9324
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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