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3-Methoxyaniline → HCID 57825031, compound

HRID 1668762
Notes
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Reaction equation

HRID 1668762 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[C:16]([CH3:23])[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.[CH3:60][O:61][C:62]1[CH:63]=[C:64]([CH:66]=[CH:67][CH:68]=1)[NH2:65]>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>[CH2:21]([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:65][C:64]4[CH:66]=[CH:67][CH:68]=[C:62]([O:61][CH3:60])[CH:63]=4)[CH:3]=3)[CH2:12][O:11][C:10]([NH2:13])=[N:9]2)=[CH:15][C:16]=1[CH3:23])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 108243-MethoxyanilineHCID 23676156Sodium t-butoxideHCID 57825006HCID 57825006, compoundHCID 67346612HCID 67346612, compound

Product 1

HCID 57825031HCID 57825031, compound

Reagents, catalysts & solvents 4

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A microwave tube was charged with 4-(3-bromo-phenyl)-4-(4-ethoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (Building Block M, 175 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 scaled 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 95 mg (30% yield) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-879def032ed348c681e98cd211836cab
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989449B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes