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4-[(5-Bromopyridin-2-yl)oxy]phenol → HCID 71227825, 화합물

HRID 2280985
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HRID 2280985 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:16][Si:17]([CH3:31])([CH3:30])[CH2:18][CH2:19][O:20][CH2:21][N:22]1[C:26](B(O)O)=[CH:25][CH:24]=[N:23]1.O.CCOC(C)=O>COCCOC.C([O-])([O-])=O.[Na+].[Na+].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>[CH3:16][Si:17]([CH3:31])([CH3:30])[CH2:18][CH2:19][O:20][CH2:21][N:22]1[C:26]([C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3)=[N:6][CH:7]=2)=[CH:25][CH:24]=[N:23]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

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HCID 129406194-[(5-Bromopyridin-2-yl)oxy]phenolHCID 21874652(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acidHCID 22728543Water ethylacetate

생성물 1

HCID 71227825HCID 71227825, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 8071
1,2-Dimethoxyethane
용매
HCID 10340Sodium Carbonate용매

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온도
100 °C

실험 절차

A suspension of Intermediate E (6.0 g, 23 mmol) and 1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-5-boronic acid (SM-2) (6.6 g, 27 mmol) in a mixture of DME (60 mL) and 2N aqueous Na2CO3 (33 mL) is sparged with Argon for 30 minutes. The mixture is treated with tetrakis(triphenylphosphine)palladium(0) (2.6 g, 2 mmol) and heated to 100° C. for 16 hours. The solution is cooled, poured into water/EtOAc, and the organic layer is collected. The aqueous layer is extracted twice with EtOAc, and the combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified on SiO2 (EtOAc/heptanes) to provide F.

후처리

  1. customis sparged with Argon for 30 minutes
  2. temperatureThe solution is cooled
  3. customthe organic layer is collected
  4. extractionThe aqueous layer is extracted twice with EtOAc
  5. washthe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified on SiO2 (EtOAc/heptanes)
  10. customto provide F

출처 및 근거

ORD 기록
ord-53916348739c4d508ea2171794da36ef
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139567B2

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