3-Iodo-N-methylpyridin-2-amine → HCID 68205837, compound

HRID 333557Notes

Reaction equation

HRID 333557 reaction equation
I[C:2]1[C:3]([NH:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:10]1([N:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[C:10]1([N:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:17]2[CH:18]=[C:19]([NH:23][C:2]3[C:3]([NH:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=3)[CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 140471463-Iodo-N-methylpyridin-2-amineHCID 21735431HCID 21735431, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68205837HCID 68205837, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A 1 L round-bottomed flask was charged with 3-iodo-N-methylpyridin-2-amine (8.95 g, 38.3 mmol), N1,N1-diphenylbenzene-1,3-diamine (9.96 g, 38.3 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (0.183 g, 0.384 mmol) and sodium 2-methylpropan-2-olate (5.15 g, 53.6 mmol) in toluene (500 mL). Nitrogen was bubbled through for 10 minutes. Then Pd2 dba3 (88 mg, 0.10 mmol) was added and this was stirred at 120° C. for overnight. The mixture was then filtered and the filtrate was concentrated and chromatographed using a mobile phase gradient of 0-20% ethyl acetate in dichloromethane to give N3-(3-(diphenylamino)phenyl)-N2-methylpyridine-2,3-diamine (12.2 g, 91% yield).

Workup

  1. customNitrogen was bubbled through for 10 minutes
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-828736f310194f469037dceba4446170
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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