3,6-Dichloropyridazine → 3-Chloro-6-(3-fluoro-4-methoxyphenyl)pyridazine

HRID 1993363ノート

反応式

HRID 1993363 の反応式
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=1>C([O-])([O-])=O.[Na+].[Na+].CCO.C1(C)C=CC=CC=1.CCOC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:13][C:14]1[N:15]=[N:16][C:17]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[CH:18][CH:19]=1

参加物

7

反応物 2

HCID 673313,6-DichloropyridazineHCID 27821943-Fluoro-4-methoxyphenylboronic acid

生成物 1

HCID 203982843-Chloro-6-(3-fluoro-4-methoxyphenyl)pyridazine

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 18778779HCID 18778779、化合物溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-fluoro-4-methoxyphenylboronic acid (10 g, 0.059 mol) and 3,6-dichloro-pyridazine (8.79 g, 0.059 mol) in 2 M Na2CO3/EtOH/toluene (80 mL/40 mL/200 mL) was bubbled through N2 for 5 min. Cat. Pd(PPh3)4 (3.47 g, 0.003 mol) was added under N2 and the reaction was heated to 80° C. for 16 h. The mixture was diluted with 200 mL of EtOAc and 40 mL of water. The organic phase was separated, washed with 80 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid obtained was washed with 50% EtOAc/hexane to provide off-white solid. MS (ESI pos. ion) m/z: 239.0 (M+H). Calc'd Exact Mass for C11H8ClFN2O: 238.65.

後処理

  1. customwas bubbled through N2 for 5 min
  2. customThe organic phase was separated
  3. washwashed with 80 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe solid obtained
  7. washwas washed with 50% EtOAc/hexane
  8. customto provide off-white solid

出典と根拠

ORDレコード
ord-8af5266fe87e48ff985cff11eec9634e
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

反応ノート

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