Triethylamine → HCID 67077953, compound

HRID 1959554Notes

Reaction equation

HRID 1959554 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:16])[C:7]=1[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1.C(N(CC)CC)C>CO.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl>[CH3:8][O:9][C:10](=[O:11])[C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([Cl:16])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 44190364HCID 44190364, compound

Product 1

HCID 67077953HCID 67077953, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,5-dichloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine (400 mg, 1.533 mmol), triethylamine (278 μL, 1.993 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II)•DCM (PdCl2(dppf)2•DCM, 63 mg, 0.077 mmol) and 4 Å molecular sieves (600 mg) in MeOH (10 mL) was stirred at 120° C. for 5 h under an atmosphere of carbon monoxide (15 bar). The reaction was filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel (elution with mixtures of hexane/EA) to give the title compound. MS (m/z): 286.0 [M+H+].

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (elution with mixtures of hexane/EA)

Sources & evidence

ORD record
ord-7e224dc24da443f98f26a01932d26fe5
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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