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Sodium Carbonate → (S)-methyl 2-(2(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxamido)propanoate

HRID 2276816
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HRID 2276816 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C@@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[O:9])[CH:5]=[C:4]([CH:17]=[CH2:18])[N:3]=1.[F:19][C:20]1[CH:41]=[CH:40][C:23]([O:24][C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][CH:26]=2)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:19][C:20]1[CH:41]=[CH:40][C:23]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:2]3[N:7]=[C:6]([C:8]([NH:10][C@@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[O:9])[CH:5]=[C:4]([CH:17]=[CH2:18])[N:3]=3)=[CH:27][CH:26]=2)=[CH:22][CH:21]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 666684382-[4-(4-Fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 89579914(S)-methyl 2-(2-chloro-6-vinylpyrimidine-4-carboxamido)propanoate

생성물 1

HCID 89580052(S)-methyl 2-(2(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxamido)propanoate수율 44%

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

To a solution of (S)-methyl 2-(2-chloro-6-vinylpyrimidine-4-carboxamido)propanoate (0.444 g, 1.65 mmol) in dioxane (10 mL) was added 2-(4-(4-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.521 g, 1.66 mmol), 2M aqueous Na2CO3 (1.65 mL, 3.30 mmol), and PdCl2(dppf) (0.071 g, 0.087 mmol). The reaction vessel was flushed with argon, sealed and heated at 100° C. overnight. After cooling, the reaction mixture was evaporated in vacuo and the residue chromatographed over silica gel with 10-40% EtOAc in hexanes. The product fractions were evaporated in vacuo to give (S)-methyl 2-(2(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxamido)propanoate as a tan-yellow oil (0.304 g, 0.72 mmol, 44% yield). LC/MS: m/z=422.2 [M+H]+.

후처리

  1. customThe reaction vessel was flushed with argon
  2. customsealed
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated in vacuo
  5. customthe residue chromatographed over silica gel with 10-40% EtOAc in hexanes
  6. customThe product fractions were evaporated in vacuo

출처 및 근거

ORD 기록
ord-73852e9c02fd4d7186ef3ed8de166c1e
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133131B2

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