3-Methoxyaniline → HCID 57825091, compound

HRID 1668764Notes

Reaction equation

HRID 1668764 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]3[CH:15]=[CH:16][C:17]4[O:21][CH2:20][CH2:19][C:18]=4[CH:22]=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.[CH3:59][O:60][C:61]1[CH:62]=[C:63]([CH:65]=[CH:66][CH:67]=1)[NH2:64]>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:21]1[C:17]2[CH:16]=[CH:15][C:14]([C:8]3([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:64][C:63]5[CH:65]=[CH:66][CH:67]=[C:61]([O:60][CH3:59])[CH:62]=5)[CH:3]=4)[CH2:12][O:11][C:10]([NH2:13])=[N:9]3)=[CH:22][C:18]=2[CH2:19][CH2:20]1

Participants

9

Reactant 4

HCID 108243-MethoxyanilineHCID 23676156Sodium t-butoxideHCID 57825048HCID 57825048, compoundHCID 67346612HCID 67346612, compound

Product 1

HCID 57825091HCID 57825091, 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-(2,3-dihydro-benzofuran-5-yl)-4,5-dihydro-oxazol-2-ylamine (Building Block K, 167 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 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 2 M ammonia in methanol. Fractions containing the compound were combined and the product purified further using preparative HPLC to yield 53 mg (30% 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-98916e27cbfa4c20a6ea632a23fbd75e
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

Loading…