3-Methoxyaniline → HCID 57825076, compound

HRID 1668765Notes

Reaction equation

HRID 1668765 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[C:16]([CH3:24])[CH:15]=3)[CH2:12][O:11][C:10]([NH2:13])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(CCC)=CC(CCC)=CC=1CCC)(C)(C)C.[CH3:61][O:62][C:63]1[CH:64]=[C:65]([CH:67]=[CH:68][CH:69]=1)[NH2:66]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OC(=O)C)C.O.C1(C)C=CC=CC=1>[CH:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:66][C:65]4[CH:67]=[CH:68][CH:69]=[C:63]([O:62][CH3:61])[CH:64]=4)[CH:3]=3)[CH2:12][O:11][C:10]([NH2:13])=[N:9]2)=[CH:15][C:16]=1[CH3:24])([CH3:23])[CH3:22]

Participants

9

Reactant 4

HCID 108243-MethoxyanilineHCID 23676156Sodium t-butoxideHCID 57825156HCID 57825156, compoundHCID 67346612HCID 67346612, compound

Product 1

HCID 57825076HCID 57825076, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A microwave tube was charged with 4-(3-bromo-phenyl)-4-(4-isopropoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (Building Block L, 181 mg, 0.467 mmol, 1.0 eq), sodium tert-butoxide (89 mg, 0.933 mmol, 2.0 eq.), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′biphenyl (18 mg, 0.042 mmol, 0.042 eq.), tris(dibenzylideneacetone)dipalladium (10 mg, 0.012 mmol, 0.025 eq.) and 3-methoxyaniline (115 mg, 0.933 mmol, 2.0 eq.). After three vacuum-nitrogen cycles, toluene was introduced (1 mL), the tube was sealed and stirred at 100° C. for 16 hours. After cooling to room temperature, water (1 mL) and ethylacetate (1 mL) were added. The organic fraction of the reaction mixture was placed on an SCX column. This was then washed with dichloromethane/methanol. The desired product was obtained by eluting with 2 M ammonia in methanol. Fractions containing the compound were combined and the product purified further using preparative HPLC to yield 99 mg (31% yield) of the title compound as a white solid.

Workup

  1. customthe tube was sealed
  2. temperatureAfter cooling to room temperature
  3. washThis was then washed with dichloromethane/methanol

Sources & evidence

ORD record
ord-01356a7a0f0447b1ba0158bf3f7891f0
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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