4-Fluorobenzoyl chloride → HCID 18931034, compound

HRID 1598957Notes

Reaction equation

HRID 1598957 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13]1[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=1>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Zn]>[Cl:19][C:14]1[C:13]([CH2:12][C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[O:7])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 189310283-(Bromomethyl)-2-chloropyridine

Product 1

HCID 18931034HCID 18931034, compoundYield 12.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred suspension of 4-fluorobenzoyl chloride (2.89 mL, 24.5 mmol), bis(triphenylphosphine)palladium (II) chloride (1.08 g, 1.54 mmol) and zinc dust (3.20 g, 49 mmol) in anhydrous dimethoxyethane (50 mL) was added a solution of the title compound of Step B (5.06 g, 24.5 mmol) in dimethoxyethane (50 mL) at room temperature under N2 over 45 min. After 20 h, the suspension was filtered through Celite® washed with ethyl acetate. The filtrate was washed with water and saturated aqueous NaCl, dried over MgSO4, and concentrated in vacuo to a yellow solid. Purification by flash chromatography eluting with 17-60% ethyl acetate/hexanes afforded the title compound of Step C as a yellow solid (0.77 g) which was somewhat impure by 1H NMR. 1H NMR (CDCl3, 300 MHz) δ8.30 (dd, 1H), 8.10 (m,2H), 7.6 (dd, 1H), 7.0-7.4 (m,3H), 4.40 (s,2H).

Workup

  1. filtrationthe suspension was filtered through Celite®
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with water and saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo to a yellow solid
  6. customPurification by flash chromatography
  7. washeluting with 17-60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3a04bc22475d463c8873508ff9d08f0a
Source dataset
uspto-grants-1998_04
Patent number
US05739326

Reaction notes

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