Sodium Carbonate → HCID 50994194, compound

HRID 1512174Notes

Reaction equation

HRID 1512174 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:5]=1[NH2:19])([O-:3])=[O:2].Br[C:21]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:22]=1[F:31].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>[F:31][C:22]1[C:21]([C:8]2[CH:7]=[CH:6][C:5]([NH2:19])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=2)=[C:26]([C:27]([F:28])([F:29])[F:30])[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5178472-Bromo-3-fluorobenzotrifluorideHCID 162179142-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 50994194HCID 50994194, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-nitro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (264 mg, 1.00 mmol, as prepared in Example 17, step A) and 2-bromo-1-fluoro-3-trifluoromethyl-benzene (243 mg, 1.00 mmol) in DME (5 mL) and 2 M aqueous Na2CO3 (4 mL, 8 mmol) was degassed via sonication, placed under argon and treated with Pd (PPh3)4 (115 mg, 0.100 mmol). The resulting mixture was heated at 80° C. for 16 h and allowed to cool to room temperature. The resulting mixture was diluted with EtOAc (10 mL) and washed twice with water (10 mL). The aqueous layer was extracted with additional EtOAc (10 mL), and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified on silica (EtOAc/hexanes, 0:100 to 50:50, v/v) to yield 6′-fluoro-3-nitro-2′-trifluoromethyl-biphenyl-4-yl-amine.

Workup

  1. customwas degassed via sonication
  2. temperatureto cool to room temperature
  3. washwashed twice with water (10 mL)
  4. extractionThe aqueous layer was extracted with additional EtOAc (10 mL)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica (EtOAc/hexanes, 0:100 to 50:50

Sources & evidence

ORD record
ord-9665b45da06d4eeab697279bf5ab8d07
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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