Potassium Phosphate, Tribasic → Methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate

HRID 1160182ノート

反応式

HRID 1160182 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH3:15].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([N:16]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:14][CH3:15])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 93237Methyl 2,6-dichloroisonicotinateHCID 235967N-propylmethanesulfonamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

生成物 1

HCID 57434730Methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A solution of methyl 2,6-dichloroisonicotinate (4.8 g, 23.3 mmol) and N-propylmethanesulfonamide (3.8 g, 28.0 mmol) in dioxane (190 mL) was degassed with argon. Potassium phosphate tribasic (6.9 g, 32.6 mmol), xantphos (810 mg, 1.40 mmol) and Pd2 dba3 (427 mg, 0.47 mmol) were added, and the reaction mixture was stirred at 100° C., sealed, for 16 h. The reaction mixture was filtered on cellite, concentrated in vacuo, and purified by flash chromatography (2×300 g silica gel, 0 to 35% EtOAc in hexane) to give methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate. 1H NMR (400 MHz, CD3OD) δ 7.87 (s, 1H), 7.72 (s, 1H), 3.97 (s, 3H), 3.91 (t, J=7.2 Hz, 2H), 3.14 (s, 3H), 1.68-1.52 (m, 2H), 0.94 (t, J=7.4 Hz, 3H).

後処理

  1. customsealed, for 16 h
  2. filtrationThe reaction mixture was filtered on cellite
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (2×300 g silica gel, 0 to 35% EtOAc in hexane)

出典と根拠

ORDレコード
ord-576a588c5d32405e9a444d5ebda2c62f
出典データセット
uspto-grants-2010_10
特許番号
US07816378B2

反応ノート

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