Lithium diisopropylamide → HCID 15488572, compound

HRID 2180257Notes

Reaction equation

HRID 2180257 reaction equation
C([N-]C(C)C)(C)C.[Li+].N[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[CH:30]=[CH:29][CH:28]=[CH:27][C:17]=1[C:18]([N:20](C(C)C)C(C)C)=[O:19]>C1COCC1>[CH:12]1[N:13]=[CH:14][CH:15]=[C:10]2[C:11]=1[C:16]1[CH:30]=[CH:29][CH:28]=[CH:27][C:17]=1[C:18](=[O:19])[NH:20]2

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamide2×HCID 10946430HCID 10946430, compound

Product 1

HCID 15488572HCID 15488572, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of lithium diisopropyl amide (LDA, 2.0 M, Aldrich, 10 mL) was dissolved in 90 mL of THF and cooled to −78° C. A solution of amine 3 (2.0 g, 6.73 mmol) in THF (25 mL) was added to the LDA dropwise over a 15 minute period. The reaction was warmed to room temperature and stirred overnight. The reaction was concentrated in vacuo and suspended in 100 mL water. The solid was filtered off and triturated with ethyl acetate (100 mL). The resulting solid was dried to yield 1.24 g (94%) of the desired compound 4. An analytical sample can be obtained by recrystallization with copious amounts of methanol. 1H NMR (DMSO): δ 9.57 (s, 1H), 8.65 (d, 1H), 8.50 (d, 1H), 8.33 (d, 1H), 7.90 (t, 1H), 7.71 (t, 1H), 7.28 (d, 1H). Anal Calcd for C12H8N2O: C, 73.46; H, 4.11; N, 14.28. Found: C, 73.53; H, 4.26; N, 14.37.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. filtrationThe solid was filtered off
  4. customtriturated with ethyl acetate (100 mL)
  5. customThe resulting solid was dried

Sources & evidence

ORD record
ord-1b1700ab045c42e0a4a1b0523a001325
Source dataset
uspto-grants-2005_05
Patent number
US06887996B2

Reaction notes

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