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

HRID 1160182노트

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HRID 1160182 반응식
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]

참가 물질

7

반응물 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)

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-576a588c5d32405e9a444d5ebda2c62f
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816378B2

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