Cesium carbonate → HCID 86703336, compound

HRID 593261Notes

Reaction equation

HRID 593261 reaction equation
[CH2:1]([N:3]([CH2:8][CH3:9])[C:4](=[O:7])[CH2:5]I)[CH3:2].[CH2:10]([NH:17][C:18]1[C:19]([F:28])=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:10]([N:17]([C:18]1[C:19]([F:28])=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21]2)[CH2:5][C:4]([N:3]([CH2:8][CH3:9])[CH2:1][CH3:2])=[O:7])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11253488Acetamide, N,N-diethyl-2-iodo-HCID 86703335HCID 86703335, compound

Product 1

HCID 86703336HCID 86703336, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As presented in the following reaction formula, N,N-diethyl-2-iodoacetamide (723 mg, 3 mmol) was added dropwise at room temperature to a mixture of 5-(benzylamino)-4-fluoro-2,3-dihydro-1H-inden-1-one (370 mg, 1.5 mmol) and cesium carbonate (Cs2CO3: 940 mg, 3 mmol) in acetonitrile (CH3CN; 20 mL). Then, the mixture was refluxed for 48 hours. The mixture was filtered and the filtrate was concentrated to give a crude product, which was purified by pre-TLC (product of Merck Co., Ltd.) to give 2-(benzyl(4-fluoro-1-oxo-2,3-dihydro-1H-inden-5-yl)amino)-N,N-diethylacetamide represented by Structural Formula (2) (5 mg, yield: 1%) as a yellow solid.

Workup

  1. temperatureThen, the mixture was refluxed for 48 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give a crude product, which
  5. customwas purified by pre-TLC (product of Merck Co., Ltd.)

Sources & evidence

ORD record
ord-8a427b495baf47ec9c2a914c32c6af1e
Source dataset
uspto-grants-2016_01
Patent number
US09242928B2

Reaction notes

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