Cesium carbonate → HCID 86638475, compound

HRID 2195518Notes

Reaction equation

HRID 2195518 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[F:16])[N:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[N:11]=[CH:10]3)=[C:4]([F:25])[CH:3]=1.[C:26](=[NH:39])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[C:33]1([C:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:39][C:2]2[CH:24]=[CH:23][C:5]([O:6][C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][C:15]=3[F:16])[N:12]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:11]=[CH:10]4)=[C:4]([F:25])[CH:3]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 66767126HCID 66767126, compound

Product 1

HCID 86638475HCID 86638475, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 5-(4-bromo-2-fluorophenoxy)-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.97 g, 2.37 mmol), benzophenone imine (0.64 g, 3.56 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.10 g, 0.075 mol), Cs2CO3 (1.16 g, 3.56 mmol), Pd2(dba)3 (0.11 g, 0.12 mmol) in 1,4-dioxane (20 mL) is purged with nitrogen, heated to 100° C. and stirred overnight. The reaction mixture is cooled to RT, extracted with EtOAc, washed with saturated aqueous sodium chloride, dried over Na2SO4, filtered and concentrated (1.45 g). MS (m/z): 510 (M+H).

Workup

  1. customis purged with nitrogen
  2. temperatureThe reaction mixture is cooled to RT
  3. extractionextracted with EtOAc
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated (1.45 g)

Sources & evidence

ORD record
ord-6b2b5985086646dbb7cbdf6718d20ebb
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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