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Methanol → Methyl 5-chloro-6-(cyclopropylmethoxy)nicotinate

HRID 2277174
Notes
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Reaction equation

HRID 2277174 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:13])[C:5]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:21][OH:22].CN([CH:26]=[O:27])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[Cl:13][C:4]1[C:5]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=[C:2]([CH:3]=1)[C:21]([O:27][CH3:26])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 867312155-Bromo-3-chloro-2-(cyclopropylmethoxy)pyridine

Product 1

HCID 86731230Methyl 5-chloro-6-(cyclopropylmethoxy)nicotinate

Reagents, catalysts & solvents 2

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-3-chloro-2-(cyclopropylmethoxy)pyridine (3.00 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (470 mg), triethylamine (3.19 mL), methanol (3 mL) and DMF (30 mL) was stirred at 80° C. for 15 hr under a carbon monoxide atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.53 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1e6d1e752ef4431ba3af2070f3c556a7
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes