Lithium diisopropylamide → HCID 57425783, compound

HRID 1360131Notes

Reaction equation

HRID 1360131 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.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29](OC)=[O:30])[N:24]=1>C1COCC1>[Br:22][C:23]1[N:24]=[C:25]([C:29](=[O:30])[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:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 147626403,3'-MethylenedipyridineHCID 16217886Methyl 6-bromopyridine-2-carboxylate

Product 1

HCID 57425783HCID 57425783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of di-3-pyridylmethane (250 mg, 1.47 mmol) in dry TIE (5 mL) was added LDA (2.1 mL, 3.16 mmol) slowly at −78° C. After 30 min a solution of methyl 2-bromopyridine-6-carboxylate (349 mg, 1.62 mmol) in dry THF (3 mL) was added slowly. After 30 min the cooling bath was removed and the mixture allowed to warm to RT. After 4 hr the mixture was diluted with saturated NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (100% EtOAc) gave 1-(6-bromopyridin-2-yl)-2,2-dipyridin-3-ylethanone as a yellow oil. 1H-NMR (500 MHz, CDCl3) δ 8.66 (m, 2 H), 8.53 (m, 2 H), 8.06 (dd, J=0.98 and 6.35 Hz, 1 H), 7.80 (m, 4 H), 7.28 (m, 2 H), 6.79 (s, 1 H).

Workup

  1. customAfter 30 min the cooling bath was removed
  2. additionAfter 4 hr the mixture was diluted with saturated NH4Cl
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2226a5efb24e4c5fb29fc3c75f2981e1
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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