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

HRID 69962

反応式

HRID 69962 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-18bd6866a86c4aa68dc5739156c49693
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

関連ノート

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