Ethyl Acetate → HCID 71150502, 화합물

HRID 407257

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HRID 407257 반응식
[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]

참가 물질

7

반응물 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

생성물 1

HCID 71150502HCID 71150502, 화합물

시약·촉매·용매 2

HCID 13169693Triphenylphosphine palladium dichloride촉매HCID 962Water용매

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온도
115 °C

실험 절차

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]−).

후처리

  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

출처 및 근거

ORD 기록
ord-acb849c9add04051938b958970a7c606
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754229B2

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