Dichloromethane → HCID 13556894, compound

HRID 464938Notes

Reaction equation

HRID 464938 reaction equation
C(N[CH2:4][CH3:5])C.[Cl:6][C:7]1[CH:25]=[CH:24][C:10]2[C:11](Br)=[CH:12][CH2:13][N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:9]=2[CH:8]=1.C([C:29]1[CH:39]=[CH:38][CH:37]=[C:31]2[C:32]([NH:34][C:35](=[O:36])[C:30]=12)=[O:33])C#C.[CH2:40](Cl)Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:6][C:7]1[CH:25]=[CH:24][C:10]2[C:11]([C:40]#[C:4][CH2:5][N:34]3[C:35](=[O:36])[C:30]4=[CH:29][CH:39]=[CH:38][CH:37]=[C:31]4[C:32]3=[O:33])=[CH:12][CH2:13][N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 132717625-Bromo-8-chloro-1-(2-fluorophenyl)-3H-2-benzazepineHCID 21953496HCID 21953496, compound

Product 1

HCID 13556894HCID 13556894, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of 40 ml of 98% diethylamine, 50 ml of methylene chloride, 0.6 g (0.9 mmole) dichlorobis(triphenylphosphine)palladium (II), 0.15 g (0.8 mmole) cuprous iodide, 3.8 g (10.8 mmole) of 8-chloro-5-bromo-1-(2-fluorophenyl)-3H-2-benzazepine and 3 g (16 mmole) of propargyl phthalimide was stirred under nitrogen at room temperature for 24 hr. The mixture was concentrated at reduced pressure to dryness. The residue was dissolved in methylene chloride and washed with water. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. Purification of the residue by column chromatography (silica gel, 50 g; eluent, methylene chloride gradient to 5% ether in methylene chloride) gave as the major fraction a colorless solid. Recrystallization from ether gave colorless needles, mp 164°-165° C.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure to dryness
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to dryness
  6. customPurification of the residue by column chromatography (silica gel, 50 g; eluent, methylene chloride gradient to 5% ether in methylene chloride)
  7. customgave as the major fraction a colorless solid
  8. customRecrystallization from ether
  9. customgave colorless needles, mp 164°-165° C.

Sources & evidence

ORD record
ord-4dacbb2caf3444b985d0f4c031d89616
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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