Lithium Hydroxide → HCID 118413256, compound

HRID 929158Notes

Reaction equation

HRID 929158 reaction equation
[Li+].[OH-].[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([NH2:29])[C:22]([N+:26]([O-:28])=[O:27])=[N:23][C:24]=1I.[Cl-].[NH4+]>O1CCOCC1.O>[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]([C:24]2[N:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:21]([NH2:29])=[CH:20][C:19]=2[Cl:18])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 90042006HCID 90042006, compound

Product 1

HCID 118413256HCID 118413256, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

LiOH (5.73 ml, 17.19 mmol) was added to a stirred mixture of 4-biphenylboronic acid (1.498 g, 7.57 mmol), 5-chloro-6-iodo-2-nitropyridin-3-amine (2.0595 g, 6.88 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.562 g, 0.688 mmol) in dioxane (15 ml)/water (4 ml) and the mixture was stirred under N2 at 80° C. for 2 h. The mixture was cooled, then aqueous ammonium chloride (saturated, 100 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic fractions were washed with brine (saturated, 80 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage™40M, eluting with 0-20% EtOAc/hexane to give the title compound. LC-MS: calculated for C17H12ClN3O2 325.06 observed m/e: 326.09 (M+H)+ (Rt 1.28/2 min).

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic fractions were washed with brine (saturated, 80 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel Biotage™40M
  8. washeluting with 0-20% EtOAc/hexane

Sources & evidence

ORD record
ord-f1b006ea4186488f99e42650bed8c910
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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