Lithium diisopropylamide → HCID 59706204, compound

HRID 1686077Notes

Reaction equation

HRID 1686077 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=1.[Li+].CC([N-]C(C)C)C.[CH3:22][N:23]([C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)[C:24]1[N:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=[O:27]>C1COCC1>[CH3:22][N:23]([C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)[C:24]1[C:25]([CH:26]([OH:27])[CH:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:28][CH:29]=[CH:30][N:31]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 147626403,3'-MethylenedipyridineHCID 77174876HCID 77174876, compound

Product 1

HCID 59706204HCID 59706204, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of bis-(3-pyridyl)methane (61 mg) in 3 mL THF was cooled to 0 C, and LDA (1.5 M in cyclohexane, 0.240 mL) was added dropwise via syringe. After the mixture had been stirred for 30 min, a solution of 2-[methyl(pyridin-3-yl)amino]nicotinaldehyde (73 mg) in 3 mL THF was added dropwise over 30 min. After 3 h stirring at 0 C, the reaction was quenched with water, then partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The aqueous solution was extracted with CH2Cl2 (2×), and the combined organic solutions were dried (Na2SO4) and purified by reverse phase HPLC to give 40 mg of 1-{2-[methyl(pyridin-3-yl)amino]pyridin-3-yl}-2,2-dipyridin-3-ylethanol.

Workup

  1. additionwas added dropwise via syringe
  2. stirringAfter 3 h stirring at 0 C
  3. customthe reaction was quenched with water
  4. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  5. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  6. dry with materialthe combined organic solutions were dried (Na2SO4)
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-58582bc2c7e04a1f81a16ca75fc009f2
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

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