Sodium Carbonate → HCID 131727401, compound

HRID 2110282Notes

Reaction equation

HRID 2110282 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[C:8]=1[F:16])(=O)=O.[C:19]([NH:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][C:28]=1[F:36])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.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>[C:22]([O:21][C:19](=[O:20])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[C:8]=2[F:16])=[CH:29][C:28]=1[F:36])([CH3:25])([CH3:23])[CH3:24]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 22288677{4-[(tert-Butoxycarbonyl)amino]-3-fluorophenyl}boronic acidHCID 57636526HCID 57636526, compound

Product 1

HCID 131727401HCID 131727401, compoundYield 92.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 7 g of 4-cyano-2,3-difluorophenyl trifluoromethanesulfonate in 400 mL of dioxane is admixed at ambient temperature with 8.67 g of N-Boc 4-amino-3-fluorophenylboronic acid, 7.235 g of sodium carbonate in solution in 100 mL of distilled water, and then 3.38 g of tetrakistriphenylphosphinepalladium. The reaction mixture is heated at 90° C. for 3 h and then concentrated to dryness under reduced pressure. The solid obtained is taken up in ethyl acetate; this organic phase is washed a number of times with distilled water and then with saturated sodium chloride solution, dried over magnesium sulfate and then concentrated to dryness under reduced pressure. The solid obtained is chromatographed on a silica column (eluent: cyclohexane/ethyl acetate, 90/10 by volume). Evaporation to dryness under reduced pressure of the fractions containing the expected product gives 7.89 g of tert-butyl(4′-cyano-3,2′,3′-trifluorobiphenyl-4-yl)carbamate in the form of a cream-white solid, whose characteristics are as follows:

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe solid obtained
  3. washthis organic phase is washed a number of times with distilled water
  4. dry with materialwith saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe solid obtained
  7. customis chromatographed on a silica column (eluent: cyclohexane/ethyl acetate, 90/10 by volume)
  8. customEvaporation to dryness under reduced pressure of the fractions
  9. additioncontaining the expected product

Sources & evidence

ORD record
ord-2b066b5b6ca74d3e8aa2298fbbd3e305
Source dataset
uspto-grants-2009_04
Patent number
US07517902B2

Reaction notes

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