Water → HCID 60209930、化合物

HRID 1497338ノート

反応式

HRID 1497338 の反応式
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH3:40])[CH:34]=1.O>C1COCC1.CCOC(C)=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>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH3:40])[CH:34]=1

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179484394-(Chloromethyl)-2-methoxypyridineHCID 60209927HCID 60209927、化合物

生成物 1

HCID 60209930HCID 60209930、化合物

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of methyl 8-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-2-carboxylate (S1) (130 mg, 0.393 mmol), Cs2CO3 (384 mg, 1.178 mmol), PdCl2(dppf)-CH2Cl2 adduct (32.1 mg, 0.039 mmol) in a microwave tube were added a solution of 4-(chloromethyl)-2-methoxypyridine (124 mg, 0.785 mmol) in THF (3 mL) followed by adding water (0.3 mL). The mixture was heated at 100° C. for 1 h. The reaction was cooled and diluted with EtOAc. The bottom H2O layer was removed. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA) to give methyl 8-fluoro-4-[(2-methoxypyridin-4-yl)methyl]quinoline-2-carboxylate (V4). ES-MS [M+1]+: 327.2.

後処理

  1. temperatureThe reaction was cooled
  2. customThe bottom H2O layer was removed
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA)

出典と根拠

ORDレコード
ord-02a5903297c2408e8e69cd5d00a58633
出典データセット
uspto-grants-2015_12
特許番号
US09199939B2

反応ノート

読み込み中…