Ethyl Acetate → HCID 71150502、化合物

HRID 407257

反応式

HRID 407257 の反応式
[NH2:1][C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[S:14][CH3:15].[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[C:19]([F:32])[C:18]=1[O:33][CH3:34].C(#N)C.O.C(OCC)(=O)C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[C:18]([O:33][CH3:34])[C:19]=2[F:32])[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[S:14][CH3:15]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 18373917Acetonitrile--water (1/1)HCID 670174932-(4-Chloro-2-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86675417Methyl 4-amino-6-chloro-5-fluoro-3-(methylthio)picolinate

生成物 1

HCID 71150502HCID 71150502、化合物

試薬・触媒・溶媒 2

HCID 13169693Triphenylphosphine palladium dichloride触媒HCID 962Water溶媒

反応条件

温度
115 °C

実験手順

Methyl 4-amino-6-chloro-5-fluoro-3-(methylthio)picolinate (300 mg, 1.2 mmol), 2-(4-chloro-2-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (450 mg, 1.6 mmol) Cesium fluoride (370 mg, 2.4 mmol) and his (triphenylphosphine) palladium (II) chloride (84 mg, 0.12 mmol) were combined in 5 ml 1:1 acetonitrile-water and heated in a microwave reactor at 115° C. for 30 m. The mixture was shaken with 30 ml ethyl acetate and 10 ml water. The org. phase was washed with 10 ml sat. NaCl, dried (Na2SO3) and evaporated. The residue was chromatographed on silica with a 0-40% ethyl acetate-hexane gradient. The gummy material was stirred with hexane to produce the written compound as a white solid, 60 mg. Mp: 113-117° C. 1H NMR (400 MHz, CDCl3) δ 7.27-7.24 (m, 2H), 5.31 (s, 2H), 3.98 (d, J=1.1 Hz, 3H), 3.96 (s, 3H), 2.32 (s, 3H). 19F NMR (376 MHz, CDCl3) δ −127.97, −128.06, −140.43, −140.52. ESIMS m/z 375 ([M+H]+), 373 ([M−H]−).

後処理

  1. washphase was washed with 10 ml sat. NaCl
  2. dry with materialdried (Na2SO3)
  3. customevaporated
  4. customThe residue was chromatographed on silica with a 0-40% ethyl acetate-hexane gradient

出典と根拠

ORDレコード
ord-acb849c9add04051938b958970a7c606
出典データセット
uspto-grants-2014_06
特許番号
US08754229B2

関連ノート

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