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Sodium Carbonate → 2-Amino-5-(2,4-dichlorophenyl)isonicotinonitrile

HRID 420498
Notes
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Reaction equation

HRID 420498 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:7](Br)=[CH:8][N:9]=1)[C:5]#[N:6].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[NH2:1][C:2]1[CH:3]=[C:4]([C:7]([C:15]2[CH:14]=[CH:13][C:12]([Cl:11])=[CH:17][C:16]=2[Cl:18])=[CH:8][N:9]=1)[C:5]#[N:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 534405772-Amino-5-bromopyridine-4-carbonitrile

Product 1

HCID 451233422-Amino-5-(2,4-dichlorophenyl)isonicotinonitrileYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-bromo-isonicotinonitrile (1.0 g, 5.1 mmol, prepared according to Example 3, Step 2.1), 2,4-dichloro-benzeneboronic acid (1.45 g, 7.6 mmol), Pd(PPh3)4 (292 mg, 0.25 mmol) and Na2CO3 (2.0 M solution in water, 8.8 mL) in DME (10 mL) was refluxed for 2 h under an inert atmosphere of argon. The reaction mixture was cooled to RT, diluted in AcOEt and washed with water. The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→3:7) to yield the title compound (880 mg, 3.3 mmol, 66%). MS: 264 [M+1]+; HPLC: AtRet=1.73; TLC: RF 0.31 (hexane/DCM/TBME 1:1:2).

Workup

  1. temperaturewas refluxed for 2 h under an inert atmosphere of argon
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→3:7)

Sources & evidence

ORD record
ord-e988434d88f840cb9b8e6bc128e7f6af
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097617B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes