Acetonitrile → HCID 18327737, compound

HRID 1250266Notes

Reaction equation

HRID 1250266 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([NH2:9])[CH:3]=1.[CH3:10][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]([CH2:14][CH:15]=[CH2:16])[CH3:13].C(N(CC)CC)C.C(#N)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:10][N:11]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH:12]([CH2:14]/[CH:15]=[CH:16]/[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([NH2:9])[CH:3]=1)[CH3:13]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 27348055-Bromo-o-toluidineHCID 15546849N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine

Product 1

HCID 18327737HCID 18327737, compoundYield 72.3%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2-aminotoluene (1.55 g, 7.17 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.71 g, 8.60 mmol ), prepared as previously described, palladium(II) acetate (16 mg, 0.07 mmol), tri-o-tolylphosphine (87 mg, 0.28 mmol), triethylamine (4.5 mL, 32.28 mmol), and acetonitrile (10 mL) was heated in a sealed glass tube at 140° C. for 14 h. The reaction mixture was cooled to ambient temperature, diluted with water (40 mL) and extracted with chloroform (4×75 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator. The crude product was purified by column chromatography on neutral alumina eluting with ethyl acetate-hexane (2:3 to 4:1) to yield 1.57 g (72.3%) of a brown liquid.

Workup

  1. customprepared
  2. extractionextracted with chloroform (4×75 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe crude product was purified by column chromatography on neutral alumina eluting with ethyl acetate-hexane (2:3 to 4:1)

Sources & evidence

ORD record
ord-7f881917e9f34299846d4f1fa905561d
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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