Potassium bis(trimethylsilyl)amide → HCID 67106787, compound

HRID 1623808Notes

Reaction equation

HRID 1623808 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:11]([C:13]1[CH:14]=[CH:15][C:16]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:17]([CH:27]=1)[C:18]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:19])=O.[C:36]([O:39][CH2:40][CH3:41])(=[O:38])[CH3:37].CCCCCC>O1CCCC1>[C:30]1([CH2:29][O:28][C:16]2[CH:15]=[CH:14][C:13](/[CH:11]=[CH:37]\[C:36]([O:39][CH2:40][CH3:41])=[O:38])=[CH:27][C:17]=2[C:18]([NH:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 21226206Ethyl acetate hexaneHCID 86668210HCID 86668210, compound

Product 1

HCID 67106787HCID 67106787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

0.5N KHMDS (1.81 ml, 0.90 mmol) was added to a solution of triethyl phosphonoacetate (0.20 g, 0.90 mmol) in tetrahydrofuran (5 ml) at −78° C. The solution was stirred at −78° C. for 15 minutes, then a suspension of 5-formyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 66; 200 mg, 0.60 mmol) in tetrahydrofuran (10 ml) was added dropwise over 3 minutes. The mixture was stirred at −78° C. for 15 minutes. It was then allowed to warm to room temperature and stirred for a further hour. The reaction was quenched with saturated NH4Cl (10 ml) and extracted with ethyl acetate (2×10 ml). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give a brown solid. Trituration with 2:1 ethyl acetate/hexane yielded the title compound as a brown solid. 160 mg.

Workup

  1. additionwas added dropwise over 3 minutes
  2. stirringThe mixture was stirred at −78° C. for 15 minutes
  3. temperatureto warm to room temperature
  4. stirringstirred for a further hour
  5. customThe reaction was quenched with saturated NH4Cl (10 ml)
  6. extractionextracted with ethyl acetate (2×10 ml)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customto give a brown solid

Sources & evidence

ORD record
ord-bbc41aa480cb4b5eb03796b8b1168e55
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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