1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59596491, compound

HRID 2264902Notes

Reaction equation

HRID 2264902 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1OS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)=[O:5])[CH3:2].[Br:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[C:36]([Cl:41])[CH:35]=1.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.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:38][C:37]1[CH:39]=[CH:40][C:34]([Br:33])=[CH:35][C:36]=1[Cl:41])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6101694-Bromo-2-chloroanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59596643HCID 59596643, compound

Product 1

HCID 59596491HCID 59596491, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A degassed solution of 1-methyl-3-(nonafluorobutane-1-sulfonyloxy)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (500 mg, 0.99 mmol), 4-bromo-2-chloroaniline (246 mg, 1.19 mmol), Pd2dba3 (91 mg, 0.10 mmol), Xantphos (114 mg, 0.20 mmol) and DBU (352 μl, 2.48 mmol) in toluene (8 ml) was subjected to microwave irradiation at 120° C. for 5 minutes. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate (100 ml). The resultant solution was washed with water (30 ml), dried (Na2SO4) and concentrated in vacuo to give an oil. The oil was purified by flash chromatography (Si-PPC, cyclohexane:ethyl acetate, gradient 90:10 to 0:100) to afford the title compound as a yellow solid (140 mg, 35%). 1H NMR (CDCl3, 400 MHz) 8.75 (d, J=1.0 Hz, 1H), 8.41 (d, J=6.1 Hz, 1H), 7.68 (s, 1H), 7.54 (d, J=2.3 Hz, 1H), 7.19-7.27 (m, 2H), 6.94 (d, J=8.8 Hz, 1H), 4.44 (q, J=7.2 Hz, 2H), 3.99 (s, 3H), 1.44 (t, J=7.2 Hz, 3H).

Workup

  1. customirradiation at 120° C. for 5 minutes
  2. washThe resultant solution was washed with water (30 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by flash chromatography (Si-PPC, cyclohexane:ethyl acetate, gradient 90:10 to 0:100)

Sources & evidence

ORD record
ord-bd6e6078c2864b9c8b5934adad3368d3
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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