Cesium carbonate → HCID 11563567, compound

HRID 2360487Notes

Reaction equation

HRID 2360487 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3Br)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][B-](F)(F)F)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCCC1.O.CC(O)=O.CC(O)=O.[Pd].C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:45][N:42]2[CH2:43][CH2:44][N:39]([C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])[CH2:40][CH2:41]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 45588144Potassium (4-tert-butoxycarbonylpiperazin-1-yl)methyltrifluoroborateHCID 58493992HCID 58493992, compound

Product 1

HCID 11563567HCID 11563567, compound

Reagents, catalysts & solvents 4

HCID 4144353Palladium (II) acetateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

8.99 g 7-bromo-1-methyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide and 5.95 g potassium ((4-(tert.-butoxycarbonyl)-piperazin-1-yl)-methyl)-trifluoroborate (for preparation see Org. Lett. 2007, 9, 1597-1600) are dissolved in 150 ml of tetrahydrofuran and 15 ml of water, combined with 17.3 g caesium carbonate and argon is piped through the resulting solution for 10 minutes. Then 120 mg palladium-II-acetate and 1.23 g 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (XPhos) are added and the mixture is heated to 80° C. for 12 hours. Then it is divided between water and ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. The crude product is further reacted directly.

Workup

  1. washthe organic phase is washed with saturated aqueous sodium chloride solution
  2. dry with materialAfter drying with magnesium sulphate the solvents
  3. customThe crude product is further reacted directly

Sources & evidence

ORD record
ord-664edadc17d64cfe8b8a3333170d3703
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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