Dimethylformamide → HCID 11372931, compound

HRID 553031Notes

Reaction equation

HRID 553031 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[CH2:17]([N:19]([CH2:23][CH3:24])[CH2:20][C:21]#[CH:22])[CH3:18].[CH2:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH3:26].[CH3:32]N(C=O)C>CCOC(C)=O.Cl[Pd-2](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>[CH2:17]([N:19]([CH2:23][CH3:24])[CH2:20][C:21]#[C:22][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([C:32]#[C:26][CH2:25][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1)[CH3:18]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 20010DietylaminopropinHCID 2599222,7-Dibromo-9-fluorenone

Product 1

HCID 11372931HCID 11372931, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418903HCID 178418903, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2,7-dibromofluoren-9-one (1.00 g, 2.97 mmol; Aldrich), 3-diethylamino-1-propyne (1.6 mL, 11.6 mmol; Lancaster), triethylamine (2 mL, 14.4 mmol; Acros), dichlorobis(triphenylphosphino)palladium (II) (Cl2Pd(PPh3)2; 90 mg, 0.13 mmol; Aldrich), and copper (I) iodide (130 mg, 0.68 mmol; Aldrich) in DMF (30 mL) was heated to 65° C. for 60 h. The reaction mixture was diluted with EtOAc, washed with water and brine, and dried over Na2SO4. The residue was purified twice by chromatography (80 g silica gel, eluting with 2-7% of 10% NH4OH/MeOH in CH2Cl2, followed by 80 g silica gel, 1-6% MeOH—CH2Cl2) to afford the title compound (1.12 g, 2.81 mmol, 95% yield). MS (DCI/NH3) m/z 399 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customThe residue was purified twice by chromatography (80 g silica gel, eluting with 2-7% of 10% NH4OH/MeOH in CH2Cl2, followed by 80 g silica gel, 1-6% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-74ec0839c19e4467aef6923fa5996501
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

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