Aniline → HCID 57824997, compound

HRID 1668771Notes

Reaction equation

HRID 1668771 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH3:23])[CH:16]=3)[CH2:13][O:12][C:11]([NH2:14])=[N:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C.[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C1(C)C=CC=CC=1>[F:8][C:6]1[CH:5]=[C:4]([C:9]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH3:23])[CH:16]=3)[CH2:13][O:12][C:11]([NH2:14])=[N:10]2)[CH:3]=[C:2]([NH:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 57825098HCID 57825098, compound

Product 1

HCID 57824997HCID 57824997, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A dried pressure tube was charged consecutively with (RS)-4-(3-bromo-5-fluoro-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (Building Block AH, 100 mg, 0.3 mmol), toluene (1.5 mL), sodium tert-butylate (52 mg, 0.5 mmol), and tert-butyl x-phos [di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine] (12 mg, 0.03 mmol). The mixture was purged with argon before [tris(dibenzylidenacetone)dipalladium chloroform complex] (8 mg, 0.008 mmol) and aniline (49 mg, 0.5 mmol) were added. The sealed tube was heated at 105° C. for 15 hours. For the working-up, the reaction mixture was cooled and evaporated under reduced pressure. The residue was directly chromatographed on an Isolute Flash NH2 column using a gradient of heptane/ethyl acetate=100/0 to 100/0 as the eluent. There were obtained 49 mg (47% of theory) of (RS)-4-(3-fluoro-5-phenylamino-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine as a white foam; Mass (calculated) C23H22FN3O2 [391]; (found) [M+H]+=392.

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was cooled
  3. customevaporated under reduced pressure
  4. customThe residue was directly chromatographed on an Isolute Flash NH2 column

Sources & evidence

ORD record
ord-bcf8cb2f64b04f8d8f6dfbb3a1b06757
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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