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Methanol → Methyl 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate

HRID 1502457
Notes
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Reaction equation

HRID 1502457 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:4][N:3]=1.F[B-](F)(F)F.F[B-](F)(F)F.C1(P(C2CCCCC2)CCCP(C2CCCCC2)C2CCCCC2)CCCCC1.[C:57](=[O:60])([O-])[O-:58].[K+].[K+].[CH3:63]O>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:6]1[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:4][N:3]=[C:2]([C:57]([O:58][CH3:63])=[O:60])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 71317487Phosphine, 1,1'-(1,3-propanediyl)bis[1,1-dicyclohexyl-, tetrafluoroborate(1-) (1:2)HCID 722214742-Chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridine

Product 1

HCID 67977255Methyl 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate
Yield 64.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (500 mg, 1.97 mmol), 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) (125 mg, 0.20 mmol), palladium(II) acetate (22 mg, 0.10 mmol), potassium carbonate (413 mg, 2.96 mmol), and methanol (1.20 mL, 29.59 mmol) in DMF (6 mL) was evacuated and then filled with nitrogen (3×), and then evacuated and filled with carbon monoxide (2×). The reaction mixture was then heated at 100° C. for 2 hours under a balloon of carbon monoxide. The cooled reaction was diluted with ethyl acetate (10 mL), filtered over Celite, and concentrated in vacuo to provide a dark red residue that was filtered through a silica plug, eluting with ethyl acetate (60 mL). The pale yellow eluent was concentrated in vacuo to afford the title compound as a yellow oil (350 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.91 (s, 1H), 4.00 (s, 3H), 2.59 (s, 3H), 1.36 (s, 12H).

Workup

  1. customwas evacuated
  2. additionfilled with nitrogen (3×)
  3. customevacuated
  4. additionfilled with carbon monoxide (2×)
  5. customThe cooled reaction
  6. filtrationfiltered over Celite
  7. concentrationconcentrated in vacuo
  8. customto provide a dark red residue that
  9. filtrationwas filtered through a silica plug
  10. washeluting with ethyl acetate (60 mL)
  11. concentrationThe pale yellow eluent was concentrated in vacuo

Sources & evidence

ORD record
ord-a4df4c98b301411da064d73cd079cb9c
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206175B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes