N,N,N',N'-Tetramethylethylenediamine → HCID 71525687, compound

HRID 1466169Notes

Reaction equation

HRID 1466169 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:22]4[C:23](=[O:26])[O:24][CH2:25][C:21]=4[CH:20]=3)[CH2:13][C:12]1=[O:29])[CH2:5]2.[CH3:30][N:31](CCN(C)C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CN(C=O)C.CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:29]=[C:12]1[CH2:13][N:14]([CH2:17][CH2:18][C:19]2[CH:28]=[CH:27][C:22]3[C:23](=[O:26])[O:24][CH2:25][C:21]=3[CH:20]=2)[CH2:15][CH2:16][N:11]1[CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:30]#[N:31])[CH:3]=2)[CH2:7]1

Participants

8

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 89526567HCID 89526567, compound

Product 1

HCID 71525687HCID 71525687, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(5-Bromo-2,3-dihydro-1H-inden-2-yl)-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one (60 mg, 0.132 mmol) in 2 mL of DMF was added Zn(CN)2 (15 mg, 0.132 mmol), Pd2(dba)3 (20 mg), TMEDA (10 mg), Xantphos (10 mg), and the mixture was stirred under microwave irradiation for 3 min at 100° C. The mixture was diluted with EtOAc and then filtrated. The filtrate was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give the title product. 1H-NMR (400 MHz, CDCl3) δ ppm 7.81 (d, J=7.8 Hz, 1H), 7.44-7.48 (m, 2H), 7.28˜7.34 (m, 3H), 5.49˜5.57 (m, 1H), 5.26 (s, 2H), 3.19˜3.28 (m, 4H), 2.88˜3.1 (m, 6H), 2.65˜2.7 (m, 4H).

Workup

  1. filtrationfiltrated
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-c7ceb43f28334ffcb3baa4065ef987fb
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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