Cesium carbonate → HCID 66893928, compound

HRID 1162004Notes

Reaction equation

HRID 1162004 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18].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.C([O-])([O-])=O.[Cs+].[Cs+]>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].C1(C)C(C)=CC=CC=1>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:18][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66053N,N-DimethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 21864764HCID 21864764, compound

Product 1

HCID 66893928HCID 66893928, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

Xylene (75 mL) was added to 7-iodo-5-nitro-1-benzofuran (1.00 g, 3.46 mmol), N,N-dimethylethane-1,2-diamine (0.37 g, 4.15 mmol), Pd2(dba)3 (0.08 g, 0.87 mmol), Xantphos (0.20 g, 0.35 mmol) and Cs2CO3 (1.59 g, 4.84 mmol). The mixture was stirred at 120° C. overnight, filtered through Celite and the solvent was removed in vacuo. The crude product was purified by flash chromatography [eluent: DCM:MeOH (6:1) and DCM:MeOH:Et3N (9:1:0.1)] to afford 0.378 g (44%) of the title compound. HPLC 90%, RT: 1.430 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 2.44 (d, J=3.22 Hz, 6H) 2.81 (t, J=6.56 Hz, 2H) 3.52 (t, J=6.56 Hz, 2H) 6.97 (d, J=2.23 Hz, 1H) 7.40 (d, J=2.23 Hz, 1H) 7.89 (t, J=1.98 Hz, 2H). LC-MS 250 (M+H)+.

Workup

  1. filtrationfiltered through Celite
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography [eluent: DCM:MeOH (6:1) and DCM:MeOH:Et3N (9:1:0.1)]

Sources & evidence

ORD record
ord-dfe7f7782502427c94741fe658e539f4
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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