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1,2-Dimethoxyethane → Methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoate

HRID 596080
Notes
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Reaction equation

HRID 596080 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)O1.Br[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:28])[CH:19]=1.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>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].C(Cl)Cl.CCCCCCC.CCOCC>[NH2:15][C:10]1[C:9]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:28])[CH:19]=2)=[CH:14][CH:13]=[CH:12][N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 22031226Methyl 4-bromo-2-methylbenzoateHCID 438110672-Aminopyridine-3-boronic acid, pinacol ester

Product 1

HCID 118046459Methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoateYield 62.1%

Reagents, catalysts & solvents 3

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 3283Diethyl EtherSolvent
HCID 8900HeptaneSolvent

Conditions

Temperature
108 °C

Procedure

To 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine(7.37 g, 33.5 mmol) in 500 mL round bottom flask were added methyl 4-bromo-2-methylbenzoate (6.390 g, 27.9 mmol), PdCl2(dppf)-DCM (2.041 g, 2.79 mmol), DME (209 mL) and 2 M Na2CO3 solution (69.7 mL). The reaction mixture was bubbled through N2 for 20 min and heated in an oil bath at 108° C. for 1.5 h. The reaction mixture was diluted with EtOAc, washed with water three times, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography eluting with 0-100% of EtOAc (containing 10% of MeOH)/heptane to provide crude product around 8 g which contained fair amount of B2(PIN)2 from previous experiment. Ether was added to dissolve the crude mixture, and then heptane was added to crush out the desired product. Solid was filtered out to provide 4.2 g of desired product with high purity in 62.1% yield. LCMS (m/z): 243.5 (MH+), 0.56 min.

Workup

  1. customThe reaction mixture was bubbled through N2 for 20 min
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with water three times
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 0-100% of EtOAc (containing 10% of MeOH)/heptane
  9. customto provide crude product around 8 g which

Sources & evidence

ORD record
ord-e08fcfd5f86c4dfaa9ca0ddc469a300a
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242996B2

Reaction notes

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