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Sodium Carbonate → 4-(2-Amino-5-chloropyridin-3-yl)phenol

HRID 2035809
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인쇄 미리보기

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HRID 2035809 반응식
C(=O)([O-])[O-].[Na+].[Na+].[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].Br[C:25]1[C:26]([NH2:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:32][C:26]1[C:25]([C:18]2[CH:17]=[CH:16][C:15]([OH:14])=[CH:20][CH:19]=2)=[CH:30][C:29]([Cl:31])=[CH:28][N:27]=1.[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:25]2[C:26]([NH2:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=2)=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)

생성물 2

HCID 667480044-(2-Amino-5-chloropyridin-3-yl)phenolHCID 667485503-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A mixture of sodium carbonate (4.09 g), tetrakis(triphenylphosphine)palladium(0) (0.668 g), 4-(tert-butyldimethylsilyloxy)phenylboronic acid (6.32 g) and 3-bromo-5-chloropyridin-2-amine (4.00 g) in DME (100 mL) and water (20 mL) was stirred at 80° C. overnight. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 4-(2-amino-5-chloropyridin-3-yl)phenol (3.05 g) as a pale yellow solid and 3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine (1.55 g) as a yellow solid.

후처리

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

출처 및 근거

ORD 기록
ord-338e77853b014eb9a4b17b887d29b64c
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575154B2

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