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Potassium Carbonate → 5-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amine

HRID 1642584
Notes
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Reaction equation

HRID 1642584 reaction equation
Br[C:2]1[CH:10]=[C:9]([NH2:11])[C:8]([O:12][CH3:13])=[C:7]2[C:3]=1[C:4]1[CH:17]=[C:16]([CH3:18])[CH:15]=[N:14][C:5]=1[NH:6]2.[CH2:19]([S:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:23])=[O:22])[CH3:20].O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=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>[CH2:19]([S:21]([C:24]1[CH:29]=[C:28]([C:2]2[CH:10]=[C:9]([NH2:11])[C:8]([O:12][CH3:13])=[C:7]3[C:3]=2[C:4]2[CH:17]=[C:16]([CH3:18])[CH:15]=[N:14][C:5]=2[NH:6]3)[CH:27]=[CH:26][CH:25]=1)(=[O:22])=[O:23])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 164271023-Ethylsulfonylphenylboronic acidHCID 588800855-bromo-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amine

Product 1

HCID 588800795-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amineYield 82%

Reagents, catalysts & solvents

2
HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A 5 mL microwave vial was charged with Compound 238 (500 mg, 1.63 mmol), 3-(ethylsulfonyl)phenylboronic acid (419 mg, 1.96 mmol) and Pd(PPh3)4 (188 mg, 0.16 mmol). To the mixture was added dioxane (5 mL) and a saturated aqueous solution of K2CO3 (2.5 mL). The reaction mixture was heated at 140° C. for 20 min. in microwave. The reaction was diluted with EtOAc and washed with aqueous water and brine. The organic extracts were dried (Na2SO4) and concentrated and purified by flash chromatography to yield the title compound (528 mg, 82%).

Workup

  1. washwashed with aqueous water and brine
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c66d1cfbdc464f5c85e49aac85a1e523
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08119655B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes