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Potassium Hydroxide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2'-chloro-4'-fluoro-5'-isopropyl-4-(methylthio)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 1994638
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HRID 1994638 반응식
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([S:26][CH3:27])[CH:23]=[CH:22][C:21]=3Br)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Cl:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([CH:40]([CH3:42])[CH3:41])=[CH:35][C:34]=1B(O)O.[OH-].[K+]>O1CCOCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([S:26][CH3:27])[CH:23]=[CH:22][C:21]=3[C:34]3[CH:35]=[C:36]([CH:40]([CH3:42])[CH3:41])[C:37]([F:39])=[CH:38][C:33]=3[Cl:32])[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 59135210(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-bromo-5-(methylthio)benzyl]-4-methyl-1,3-oxazolidin-2-oneHCID 66716668(2-Chloro-4-fluoro-5-isopropylphenyl)boronic acid

생성물 1

HCID 11685920(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2'-chloro-4'-fluoro-5'-isopropyl-4-(methylthio)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 312751,4-Dioxane용매

실험 절차

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-bromo-5-(methylthio)benzyl]-4-methyl-1,3-oxazolidin-2-one (60 mg, 0.114 mmol) in 1,4-dioxane (1 mL) was added (2-chloro-4-fluoro-5-isopropylphenyl)boronic acid (10 mg, 0.12 mmol), [1,1′-bis(diphenylphosphino) ferrocene] dichloropalladium (II) (28 mg, 30 mol %) and aqueous potassium hydroxide (95 μL, 3M, 2 eq.). The reaction mixture was purged with nitrogen and then sealed in a microwave vessel. The reaction vessel was subject to microwave irradiation at 150° C. for 30 min. Crude mixture was worked up with water and EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude product. This was purified by preparative TLC plate to afford the titled compound. LC-MS: 619.95 (M+1)+. 1H NMR (CDCl3, 500 MHz) a 1:1 mixture of rotamers δ 7.83-7.88 (m, 1H), 7.72 (s, 1H) 7.68 (s, 1H), 7.30-7.35 (m, 1H), 7.24-7.29 (m, 1H), 7.11-7.19 (m, 2.5H), 7.04-7.07 (m, 0.5H), 5.62 (d, J=8.2 Hz, 0.5H), 5.24 (d, J=8.0 Hz, 0.5H), 4.87 (d, J=15.3 Hz, 0.5H), 4.70 (d, J=15.8 Hz, 0.5H), 3.79-3.98 (m, 2H), 3.18 (m, 1H), 2.55 (s, 1.5H), 2.54 (s, 1.5H), 1.20-1.29 (m, 6H), 0.53 (d, J=6.4 Hz, 1.5H), 0.47 (d, J=6.6 Hz, 1.5H).

후처리

  1. customThe reaction mixture was purged with nitrogen
  2. customsealed in a microwave vessel
  3. customirradiation at 150° C. for 30 min
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by preparative TLC plate

출처 및 근거

ORD 기록
ord-a054b9aa83cb4a2082dc51780e30975d
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07652049B2

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