Lithium diisopropylamide → HCID 57795054, compound

HRID 2099576Notes

Reaction equation

HRID 2099576 reaction equation
N1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)C=1.[Li+].C[CH:16]([N-:18]C(C)C)C.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Br:37])[N:32]=2)Cl)[N:24]=1>C1COCC1>[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Br:37])[N:32]=2)[CH:7]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:16][N:18]=2)[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:24]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 147626403,3'-MethylenedipyridineHCID 86094276HCID 86094276, compound

Product 1

HCID 57795054HCID 57795054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 3-(pyridin-3-ylmethyl)pyridine (0.085 g, 0.5 mmol) in THF (5 mL) at −78° C. was added LDA (0.3 mL, 1.8 M) and stirred for 1 h. 2-Bromo-6-[(6-bromopyridin-2-yl)(chloro)methyl]pyridine (0.181 g, 0.5 mmol) in THF (2 mL) was added. The mixture was stirred at 0° C. for 1 h. The reaction was quenched with ice and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (50% EtOAc in hexane) to give 2-bromo-6-[1-(6-bromopyridin-2-yl)-2-pyridin-2-yl-2-pyridin-3-ylethyl]pyridine. 1H-NMR (500 MHz, CDCl3) δ 8.58 (d, 1H, J=1.9), 8.47 (d, 1H, J=4.9), 8.30 (dd, 1H, J=4.7, 1.5), 7.95 (d, 1H, J=8.1), 7.44 (td, 1H, J=7.6, 1.7), 7.39 (t, 2H, J=7.7), 7.28-7.33 (m, 2H), 7.20 (d, 1H, J=7.6), 7.15 (dd, 2H, J=7.7, 4.7), 7.10 (dd, 1H, J=7.9, 4.8), 6.97 (dd, 1H, J=7.4, 4.8), 5.45 (d, 1H, J=12.0), 5.29 (d, 1H, J=12.0). LRMS m/z (M+H) Calcd: 497.2, found: 496.9.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. customThe reaction was quenched with ice
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid
  8. customThe solid was purified by silica gel chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-319b56699d064741ba18ba8a1de70998
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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