2,6-Difluorophenylboronic acid → Methyl 3-amino-6-(2,6-difluorophenyl)picolinate

HRID 69962

Reaktionsgleichung

Reaktionsgleichung von HRID 69962
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1B(O)O>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.COCCOC>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:15]2[C:14]([F:13])=[CH:19][CH:18]=[CH:17][C:16]=2[F:20])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 27343362,6-Difluorophenylboronic acidHCID 45480453Methyl 3-amino-6-bromopyridine-2-carboxylate

Produkt 1

HCID 59226548Methyl 3-amino-6-(2,6-difluorophenyl)picolinateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 3-amino-6-bromopicolinate (1.0 equiv.), 2,6-difluorophenyl-boronic acid (3.0 equiv), and Pd(dppf)Cl2-DCM (0.1 equiv.) in 3:1 DME/2M Na2CO3 (0.5M) was subjected to microwave irradiation at 120° C. for 15 min intervals. The reaction was filtered and washed with EtOAc. The organic was partitioned with H2O (25 mL), was further washed with NaCl(sat.) (25 mL), was dried over MgSO4, and the volatiles were removed in vacuo. The residue was diluted in EtOAc and passed through a silica gel plug and the volatiles were removed in vacuo yielding methyl 3-amino-6-(2,6-difluorophenyl)picolinate (47%). LCMS (m/z): 265.1 (MH+); LC Rt=2.70 min.

Aufarbeitung

  1. customirradiation at 120° C. for 15 min intervals
  2. filtrationThe reaction was filtered
  3. washwashed with EtOAc
  4. customThe organic was partitioned with H2O (25 mL)
  5. washwas further washed with NaCl(sat.) (25 mL)
  6. dry with materialwas dried over MgSO4
  7. customthe volatiles were removed in vacuo
  8. additionThe residue was diluted in EtOAc
  9. customthe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-18bd6866a86c4aa68dc5739156c49693
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822497B2

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