Triethylamine → HCID 67334619, compound

HRID 1669649Notes

Reaction equation

HRID 1669649 reaction equation
FC1C=C(C=CC=1)CO[C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)[CH2:18][CH2:17][CH:16]([C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38].C(N(CC)CC)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:21][C:19]([F:22])([F:20])[CH:16]1[CH2:15][CH2:14][C:13]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)([C:10]2[CH:9]=[CH:8][C:7]([C:41]#[C:40][Si:37]([CH3:39])([CH3:38])[CH3:36])=[CH:12][CH:11]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 67332436HCID 67332436, compound

Product 1

HCID 67334619HCID 67334619, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the title compound from Example 2, step A (200 mg, 0.39 mmol) in 1.2 mL of DMF was added trimethylsilylacetylene (0.085 mL, 0.59 mmol), bis(triphenylphosphine)palladium (II) chloride (83 mg, 0.12 mmol) and triethylamine (0.27 mL, 2.0 mmol). The mixture was stirred at 70° C. under N2 for 1 hour and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a gradient of 0% to 20% EtAOc/hexanes to provide the title compound. LC-MS (ESI): m/z=459.4 [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with a gradient of 0% to 20% EtAOc/hexanes

Sources & evidence

ORD record
ord-305b22436d2741a289c413c664e680c9
Source dataset
uspto-grants-2011_08
Patent number
US07989472B2

Reaction notes

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