4-Fluorobenzaldehyde → HCID 57425775, compound

HRID 1360127Notes

Reaction equation

HRID 1360127 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.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>C1COCC1>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]([OH:28])[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:25][CH:24]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 2724682Lithium diisopropylamideHCID 147626403,3'-Methylenedipyridine

Product 1

HCID 57425775HCID 57425775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 3-(pyridin-3-ylmethyl)pyridine (0.195 g, 1.15 mmol) in THF (5 mL) at −78° C. was added LDA (0.7 mL, 1.8 M) and stirred for 1 h. 4-Fluorobenzaldehyde (0.171 g, 1.37 mmol) in THF (1 mL) was added. The mixture was stirred at −78° C. for 10 min and at −45° C. for 0.5 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 triturated with CH2Cl2 to give 1-(4-fluorophenyl)-2,2-dipyridin-3-ylethanol. 1H-NMR (500 MHz, CDCl3) δ 8.60 (d, 1H, J=1.7), 8.45 (d, 1H, J=1.9), 8.38 (dd, 1H, J=4.7, 1.2), 8.27 (dd, 1H, J=4.6, 1.2), 7.91 (d, 1H, J=7.8), 7.76 (d, 1H, J=8.0), 7.34-7.29 (m, 3H), 7.19 (dd, 1H, J=7.8, 4.9), 7.02 (t, 2H, J=8.8), 5.68 (d, 1H, J=4.9), 5.45 (dd, 1H, J=8.5, 4.8), 4.34 (d, 1H, J=8.8). LRMS m/z (M+H) Calcd: 295.3. found: 295.1.

Workup

  1. stirringThe mixture was stirred at −78° C. for 10 min and at −45° C. for 0.5 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 triturated with CH2Cl2

Sources & evidence

ORD record
ord-2c8655e4df114115a7c1c21b29a8c85c
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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