Cesium carbonate → HCID 68093911, compound

HRID 573309Notes

Reaction equation

HRID 573309 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:19]4=[N:20][CH:21]=[CH:22][CH:23]=[C:18]4[N:17]([CH2:24][CH3:25])[N:16]=3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:26]B(O)O.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>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH2:24]([N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:26])=[CH:7][N:6]=3)=[CH:10][CH:11]=2)=[N:16]1)[CH3:25]

Participants

9

Reactant 4

HCID 10796Cesium carbonate2×HCID 139377Methylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66728118HCID 66728118, compound

Product 1

HCID 68093911HCID 68093911, compoundYield 20.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of 3-[4-(5-chloropyridin-2-yloxy)phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine (58 mg), methylboronic acid (59.4 mg), Pd(dppf)2Cl2 (18 mg) and Cs2CO3 (766 mg) in DME/H2O (4 mL, 3/1) was exposed to microwave irradiation at 140° C. for 1 h, and then Pd(OAc)2 (3.7 mg), Xphos (15.7 mg) and Cs2CO3 (107 mg) were added. The mixture was exposed to microwave irradiation at 140° C. for 1 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC (H2O in CH3CN containing 10 mM NH4HCO3). Crystallization from AcOEt/hexane gave title compound (11 mg).

Workup

  1. customirradiation at 140° C. for 1 h
  2. customirradiation at 140° C. for 1 h
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC (H2O in CH3CN containing 10 mM NH4HCO3)
  7. customCrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-b9bac3a8dc234404a187e40c4cd068b5
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…