1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59596638, compound

HRID 2264895Notes

Reaction equation

HRID 2264895 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]([F: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[F:41])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1230504-Bromo-2-fluoroanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59596643HCID 59596643, compound

Product 1

HCID 59596638HCID 59596638, compoundYield 34%

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 (800 mg, 1.58 mmol), 4-bromo-2-fluoroaniline (360 mg, 1.89 mmol), Pd2dba3 (144 mg, 0.16 mmol), Xantphos (182 mg, 0.32 mmol) and DBU (538 μl, 3.79 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 (50 ml), dried over sodium sulfate and concentrated in vacuo to give a solid residue. The solid residue was purified by flash chromatography (Si-PPC, pentane:ethyl acetate, gradient 100:0 to 60:40) to afford the title compound as a yellow solid (210 mg, 34%). LCMS (method B): RT=2.33 min, M+H=392/394.

Workup

  1. customirradiation at 120° C. for 5 minutes
  2. washThe resultant solution was washed with water (50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a solid residue
  6. customThe solid residue was purified by flash chromatography (Si-PPC, pentane:ethyl acetate, gradient 100:0 to 60:40)

Sources & evidence

ORD record
ord-b9b5a630da7f49e0a66eb588aceb8acf
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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