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

HRID 2280985
Notes
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Reaction equation

HRID 2280985 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

HCID 71227825HCID 71227825, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent
HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-53916348739c4d508ea2171794da36ef
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139567B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes