Water → HCID 135870271, compound

HRID 883178Notes

Reaction equation

HRID 883178 reaction equation
C[Al](C)C.[CH3:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:14][C:15]1[CH:16]=[C:17]([C:23]2[O:27][N:26]=[C:25]([C:28]([O:30]C)=O)[CH:24]=2)[CH:18]=[C:19]([Br:22])[C:20]=1[OH:21].O>CCCCCC.C(Cl)(Cl)Cl>[CH2:7]([N:6]([CH3:5])[C:28]([C:25]1[CH:24]=[C:23]([C:17]2[CH:18]=[C:19]([Br:22])[C:20]([OH:21])=[C:15]([Br:14])[CH:16]=2)[O:27][N:26]=1)=[O:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7669N-MethylbenzylamineHCID 16682925TrimethylaluminumHCID 135995333HCID 135995333, compound

Product 1

HCID 135870271HCID 135870271, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8058HexaneSolvent

Procedure

Trimethylaluminium (0.1 mL of a 2 N solution in hexane, 0.2 mmol) was added to a solution of N-methylbenzylamine (27 mg, 0.22 mmol) in dry chloroform (2 mL) under nitrogen and the resulting solution was stirred at room temperature for 20 minutes. Methyl 5-(3,5-dibromo-4-hydroxyphenyl)isoxazole-3-carboxylate (75 mg, 0.2 mmol) was added and the reaction mixture was stirred at 50° C. for 48 hours. Water (1 mL) and chloroform (2 mL) were added to the solution; the chloroform was separated and evaporated to dryness. The residue was dissolved in dimethylsulphoxide (1 mL) and purified by preparative HPLC to give the title compound (42.8 mg, 46%) as a colorless powder. 1H NMR δ (ppm) (DMSO-d6): 2.96 and 3.09 (3 H, two s), 4.76 (2 H, s), 7.28-7.46 (6 H, m), 8.14 and 8.16 (2 H, t, two s), 10.73 (1 H, s). LCMS (10 cm_apci_formic) Rt 3.79 min; m/z 463/465/467 [M−H]−.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 48 hours
  2. customthe chloroform was separated
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in dimethylsulphoxide (1 mL)
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-47a734d54efc4195b2d041b337db7866
Source dataset
uspto-grants-2012_08
Patent number
US08236838B2

Reaction notes

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