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Potassium Carbonate → HCID 86689303, compound

HRID 1852489
Notes
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Reaction equation

HRID 1852489 reaction equation
O([C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]=1[N+:19]([O-:21])=[O:20])S(C(F)(F)F)(=O)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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.C1(C)C=CC=CC=1>[N+:19]([C:10]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16]=2[CH:17]=[CH:18][C:9]=1[NH:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27])([O-:21])=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 167023-AminobenzonitrileHCID 86689304HCID 86689304, compound

Product 1

HCID 86689303HCID 86689303, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

An anhydrous toluene (30 mL) suspension of 1-nitro-5,6,7,8-tetrahydronaphthalen-2-yl triflate (1.95 g, 6.00 mmol), 3-aminobenzonitrile (1.06 g, 9.00 mmol), potassium carbonate (830 mg, 6.00 mmol), tetrakis(triphenylphosphine)palladium (346 mg, 0.30 mmol), and triphenylphosphine (158 mg, 0.60 mmol) was stirred at 110° C. for 18 hours. The reaction mixture was cooled on standing, and filtered. The filtrate was diluted with ethyl acetate. The obtained organic solution was washed with purified water, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give the titled compound as orange powder (1.515 g, yield 86%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additionThe filtrate was diluted with ethyl acetate
  4. washThe obtained organic solution was washed with purified water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-3cb108f9fb234edaa689835b2f26916f
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962613B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes