1,10-Phenanthroline → HCID 131735187, compound

HRID 623677Notes

Reaction equation

HRID 623677 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:21]=[CH:20][C:10]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Br[C:23]#[C:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Na+].[Cl-].[NH4+].[OH-]>C1(C)C=CC=CC=1.[Cu]I.CCOCC>[C:15]([O:14][C:13](=[O:19])[N:12]([CH2:11][C:10]1[CH:20]=[CH:21][C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:8][CH:9]=1)[C:23]#[C:24][Si:25]([CH:26]([CH3:28])[CH3:27])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])([CH3:16])([CH3:17])[CH3:18]

Participants

9

Reactant 5

HCID 13181,10-PhenanthrolineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11196280(2-Bromoethynyl)tris(propan-2-yl)silaneHCID 59746539HCID 59746539, compoundHCID 131735185HCID 131735185, compound

Product 1

HCID 131735187HCID 131735187, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of t-butyl 4-morpholinobenzylcarbamate (1.11 g, 3.80 mmol), bromoethynyl-triisopropyl-silane, CuI (225 mg, 1.17 mmol) and 1,10-phenantroline (250 mg, 1.40 mmol) in dry toluene (7.5 ml) was warmed to 90° C. under a nitrogen atmosphere. KHMDS (10 ml, 0.5 M in toluene) was added dropwise under nitrogen atmosphere and the mixture was stirred for 12 hours at this temperature. The reaction mixture was cooled to RT; Et2O (30 ml) and NaCl/NH4OH (60/30 ml) were added and the organic phase was extracted with Et2O (3×30 ml), washed with NaCl/NH4 and dried over Na2SO4. The solvent was removed under reduced pressure to afford the title compound which was purified by column chromatography (PE/AcOEt:95/5).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionthe organic phase was extracted with Et2O (3×30 ml)
  3. washwashed with NaCl/NH4
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f5983b722ef418ebce8aaaf9318a9e9
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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