Cesium carbonate → HCID 58063592, compound

HRID 2035703Notes

Reaction equation

HRID 2035703 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[N:9]=[N:10][N:11]([CH:13]3[CH2:19][CH2:18][C:17]4[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:14]3=[O:30])[CH:12]=2)=[N:6][CH:7]=1.[N:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CCOC(C)=O.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].O1CCOCC1.O>[F:24][C:20]1[C:17]2[CH2:18][CH2:19][CH:13]([N:11]3[CH:12]=[C:8]([C:5]4[N:4]=[CH:3][C:2]([C:34]5[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=5)=[CH:7][N:6]=4)[N:9]=[N:10]3)[C:14](=[O:30])[N:15]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:16]=2[CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66684138HCID 66684138, compound

Product 1

HCID 58063592HCID 58063592, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[4-(5-Bromopyrimidin-2-yl)-1H-1,2,3-triazol-1-yl]-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (75 mg, 0.155 mmol), 4-pyridineboronic acid (28.5 mg, 0.232 mmol), Pd2(dba)3 (7.08 mg, 7.73 μmol), cesium carbonate (101 mg, 0.309 mmol), and X-phos (7.37 mg, 0.015 mmol) were combined in a microwave vial along with water (0.5 mL) and 1,4-dioxane (0.9 mL). The vessel was irradiated for 15 mins at 140° C. The vial was allowed to cool before being diluted with EtOAc and syringe filtered. The filtrate was concentrated and purified on column chromotagraphy to yield the desired product, 11 mg.

Workup

  1. customThe vessel was irradiated for 15 mins at 140° C
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified on column chromotagraphy

Sources & evidence

ORD record
ord-457eeaa60978441d97786d2e44a380c9
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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