1,3-Benzodioxol-5-amine → HCID 57825008, compound

HRID 1668761Notes

Reaction equation

HRID 1668761 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][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.[CH2:56]1[O:65][C:64]2[CH:63]=[CH:62][C:60]([NH2:61])=[CH:59][C:58]=2[O:57]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[O:65]1[C:64]2[CH:63]=[CH:62][C:60]([NH:61][C:2]3[CH:3]=[C:4]([C:8]4([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[CH2:12][O:11][C:10]([NH2:13])=[N:9]4)[CH:5]=[CH:6][CH:7]=3)=[CH:59][C:58]=2[O:57][CH2:56]1

Participants

9

Reactant 4

HCID 843101,3-Benzodioxol-5-amineHCID 23676156Sodium t-butoxideHCID 57825045HCID 57825045, compoundHCID 67346612HCID 67346612, compound

Product 1

HCID 57825008HCID 57825008, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

An oven dried pressure tube was charged with (RS)-4-(3-bromo-phenyl)-4-phenyl-4,5-dihydro-oxazol-2-ylamine (Building Block A, 100 mg, 0.315 mmol), sodium tert-butoxide (61 mg, 0.63 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′biphenyl (12 mg, 0.028 mmol), tris(dibenzylideneacetone)dipalladium (7 mg, 0.008 mmol) and 3,4-(methylendioxy)-aniline (86 mg, 0.631 mmol). After three vacuum-nitrogen cycles, toluene was introduced (0.7 mL), the tube was scaled and stirred at 100° C. for 16 hours. After cooling to room temperature, water (1 mL) and ethyl acetate (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 2M ammonia in methanol. Fractions containing the compound were combined and the product purified further using preparative HPLC to yield 32 mg (26% yield) of the title compound as a white solid.

Workup

  1. customAn oven dried pressure tube
  2. temperatureAfter cooling to room temperature
  3. washThis was then washed with dichloromethane/methanol

Sources & evidence

ORD record
ord-928fe12860344940bee8e5e0007dca6d
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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