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Hexane → HCID 117700526, compound

HRID 873527
Notes
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Reaction equation

HRID 873527 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[O:10])=[C:7]([CH3:11])[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=1.[CH2:21]([O:28][C:29]1[C:30]([C:36]([O:38][CH3:39])=[O:37])=[N:31][C:32](Br)=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].CCCCCC>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>[CH2:21]([O:28][C:29]1[C:30]([C:36]([O:38][CH3:39])=[O:37])=[N:31][C:32]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([CH:9]=[O:10])[C:7]=2[CH3:11])=[CH:33][CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 59418684Methyl 3-(benzyloxy)-6-bromopicolinateHCID 130141572HCID 130141572, compound

Product 1

HCID 117700526HCID 117700526, compoundYield 112%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent2×
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of the 6-methoxy-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde produced in Example 4-1 (1.91 g, 6.92 mmol), methyl 3-(benzyloxy)-6-bromopyridine-2-carboxylate (PCT Int. Appl., 2010080478, 15 Jul. 2010) (2.23 g, 6.92 mmol), sodium carbonate (2.20 g, 20.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.40 g, 0.35 mmol) in 1,2-dimethoxyethane (38 ml) and water (17 ml) was prepared at room temperature, and the suspension thus prepared was then stirred at 90° C. for 3 hours. After air-cooling, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (ethyl acetate:hexane=2:3, v/v) to obtain the title compound (3.02 g, yield: 112%).

Workup

  1. customwas prepared at room temperature
  2. customthe suspension thus prepared
  3. temperatureAfter air-cooling
  4. extractionthe mixed solution was then extracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue thus obtained
  9. customwas then purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-f7f2795732ee4044ab17e4f7f4d00039
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08975263B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes