1,10-Phenanthroline → (4-Morpholin-4-yl-phenyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid tert-butyl ester

HRID 623672Notes

Reaction equation

HRID 623672 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Br[C:22]#[C:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26].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:16]([O:15][C:14](=[O:20])[N:13]([C:10]1[CH:9]=[CH:8][C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:12][CH:11]=1)[C:22]#[C:23][Si:24]([CH:25]([CH3:27])[CH3:26])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])([CH3:17])([CH3:19])[CH3:18]

Participants

9

Reactant 5

HCID 13181,10-PhenanthrolineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11196280(2-Bromoethynyl)tris(propan-2-yl)silaneHCID 11482840tert-Butyl [4-(morpholin-4-yl)phenyl]carbamateHCID 131735185HCID 131735185, compound

Product 1

HCID 131735184(4-Morpholin-4-yl-phenyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid tert-butyl esterYield 40%

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-morpholinophenylcarbamate (1.45 g, 7.60 mmol), bromoethynyl-triisopropyl-silane, CuI (450 mg, 2.34 mmol) and 1,10-phenantroline (500 mg, 2.80 mmol) in dry toluene (15 ml) was warmed up to 90° C. under a nitrogen atmosphere. KHMDS (20 ml, 0.5 M in toluene) was added dropwise under nitrogen and the mixture was stirred for 12 hours at this temperature. The reaction was cooled down 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 and the title compound was obtained after purification by column chromatography (PE/AcOEt: 95/5).

Workup

  1. temperatureThe reaction was cooled down 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-d61fd1e97bff4e30ba7fa4966a0c6859
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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