Potassium Carbonate → Ammonium Hydroxide

HRID 657355Notes

Reaction equation

HRID 657355 reaction equation
Cl.Br[C:3]1[CH:4]=[C:5]([CH2:10][NH2:11])[CH:6]=[CH:7][C:8]=1[F:9].[OH:12][CH2:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[NH4+:11].[OH-:12].[NH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:13][OH:12])[CH:19]=2)[CH:4]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27249011-(3-Bromo-4-fluorophenyl)methanamine hydrochlorideHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 57813296[5'-(Aminomethyl)-2'-fluoro-3-biphenylyl]methanol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

[(3-Bromo-4-fluorophenyl)methyl]amine hydrochloride (0.795 g, 3.29 mmol), [3-(hydroxymethyl)phenyl]boronic acid (0.5 g, 3.29 mmol), potassium carbonate (2.275 g, 16.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.114 g, 0.1 mmol) were combined in dioxane (10 mL) and water (3 mL). The mixture was microwaved at 150° C. for 30 min. The solvents were evaporated and the residue taken up in EtOAc and H2O. The aqueous phase was extracted 2× with EtOAc. The combined organic phases were dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by CombiFlash on a silica gel column eluting with 0-100% CH2Cl2/CH2Cl2: 20% MeOH:1% NH4OH to afford the title compound as a viscous oil. LC-MS m/z 231.8 (M+H)+, 1.03 min (ret time).

Workup

  1. customThe mixture was microwaved at 150° C. for 30 min
  2. customThe solvents were evaporated
  3. extractionThe aqueous phase was extracted 2× with EtOAc
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by CombiFlash on a silica gel column
  8. washeluting with 0-100% CH2Cl2/CH2Cl2

Sources & evidence

ORD record
ord-ff1cf993c9da477b84320881f0b0589a
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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