Ethyl bromoacetate → HCID 58497208, compound

HRID 1254073Notes

Reaction equation

HRID 1254073 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:19]=[CH:18][N:17](CC)[N:16]=3)=[N:11][C:10]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3N=CO[N:29]=3)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:35][CH2:36][O:37][C:38]([CH2:40]Br)=[O:39]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:19]=[CH:18][N:17]([CH2:40][C:38]([O:37][CH2:36][CH3:35])=[O:39])[N:16]=3)=[N:11][C:10]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 58497238HCID 58497238, compound

Product 1

HCID 58497208HCID 58497208, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of Step 2 product of Example 140 (100 mg, 0.255 mmol) in THF (2 ml) at 0° C. was added NaH (20.4 mg, 0.510 mmol). After stirred at 0° C. for 1 hr, ethyl bromo acetate (0.034 ml, 0.306 mmol) was added and then stirred at 0° C. for one hour. Reaction mixture was quenched with water, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, concentrated, separated by prep. TLC (Hex:EtOAc=2:1) to give ethyl (3-{5-[(4-chlorophenyl)sulfanyl]-4-(4-cyanophenyl)-1-methyl-1H-imidazol-2-yl}-1H-pyrazol-1-yl)acetate (70 mg) desired compound. LCMS: [M+1]+=478.0.

Workup

  1. stirringstirred at 0° C. for one hour
  2. customReaction mixture
  3. customwas quenched with water
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customseparated by prep

Sources & evidence

ORD record
ord-1783316d87e045b1a810162ec2b6da86
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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