1-Ethynyl-3-methoxybenzene → HCID 53690642, compound

HRID 1607021Notes

Reaction equation

HRID 1607021 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]3[CH2:19][CH2:18][CH2:17][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3I)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C:29]#[CH:30])[CH:26]=[CH:27][CH:28]=1>C(NCC)C.CN(C)C=O.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.[Cu]I>[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]3[CH2:19][CH2:18][CH2:17][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:30]#[C:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 6407531-Ethynyl-3-methoxybenzeneHCID 18634703HCID 18634703, compound

Product 1

HCID 53690642HCID 53690642, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8021DiethylamineSolvent

Procedure

2.0 g (5 mmol) (S)-8-chloro-11,12,13,13a-tetrahydro-1-iodo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was heated to boiling under reflux for 9 hours with 0.73 g (5.6 mmol) of 3-methoxyphenylacetylene, 65 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 65 mg of copper(I) iodide in 20 ml of diethylamine and 20 ml of N,N-dimethylformamide. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with methylene chloride/methanol (99:1). By crystallization from methylene chloride and ethyl acetate there was obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-[(m-methoxyphenyl)ethynyl]-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 204°-205°.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on silica gel
  3. washwhile eluting with methylene chloride/methanol (99:1)
  4. customBy crystallization from methylene chloride

Sources & evidence

ORD record
ord-16de0f6b37b84c96b3bbb2cd3f81ec25
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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