Dichloromethane → HCID 86695502, 화합물

HRID 525614노트

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HRID 525614 반응식
[F:1][CH:2]([F:29])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:28])[CH3:27])=[O:4].Br[C:31]1[CH:32]=[CH:33][C:34]([CH:37]([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH3:38])=[N:35][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O1CCOCC1.O>[F:29][CH:2]([F:1])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:31]3[CH:32]=[CH:33][C:34]([CH:37]([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH3:38])=[N:35][CH:36]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:28])[CH3:27])=[O:4]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 866954142,2-difluoro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-3-yl)ethanoneHCID 86695503benzyl N-[1-(5-bromopyridin-2-yl)ethyl]carbamate

생성물 1

HCID 86695502HCID 86695502, 화합물

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of the product of Example 22, Step 3, benzyl (1-(5-bromopyridin-2-yl)ethyl)carbamate, 2.0M sodium carbonate in water (3.1 mL, 6.2 mmol) in dioxane is degassed with nitrogen. 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium(ii) complex with dichloromethane (169 mg, 0.21 mmol) is added and the mixture heated to 80° C. overnight. After cooling to room temperature the reaction mixture is diluted with water (25 mL) and extracted with ethylacetate. The organic phase is separated, dried over MgSO4, and concentrated under reduced pressure. The crude material is purified using silica chromatography eluting from 25% ethylacetate/heptane to 35% ethylacetate/heptane to give the title product (1.00 g): m/z: 541.22.

후처리

  1. customis degassed with nitrogen
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. extractionextracted with ethylacetate
  4. customThe organic phase is separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material is purified
  8. washeluting from 25% ethylacetate/heptane to 35% ethylacetate/heptane

출처 및 근거

ORD 기록
ord-f651b4d2300542fc8ec169d7e4a39f40
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340564B2

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