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

HRID 69962
Notes
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Reaction equation

HRID 69962 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-Dimethoxyethane
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-18bd6866a86c4aa68dc5739156c49693
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822497B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes