Potassium Phosphate, Tribasic → HCID 67518058, compound

HRID 1465716Notes

Reaction equation

HRID 1465716 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=1.[N:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32](B4OC(C)(C)C(C)(C)O4)[CH:33]=3)[N:28]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[N:27]=2)=[CH:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[N:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:2]4[CH:3]=[N:4][N:5]([CH:7]5[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]5)[CH:6]=4)[CH:33]=3)[N:28]([C:44]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[N:27]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 67027251HCID 67027251, compoundHCID 67518406HCID 67518406, compound

Product 1

HCID 67518058HCID 67518058, compoundYield 30.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To tert-butyl 3-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylate (0.66 g, 2 mmol) and 3-(pyridin-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-indazole (1.13 g, 2 mmol) in dioxane (8 mL) and water (2 mL) was added potassium phosphate (848 mg, 4 mmol) and PdCl2(dppf) (120 mg, 0.16 mmol). The reaction mixture was stirred at 80° C. for 24 h. After filtered through a pad of celite, and washed with EtOAc, the filtrate was washed with brine, dried and concentrated. The crude mixture was column purified with mixture of methanol, dichloromethane and ammonia to give tert-butyl 3-(4-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (420 mg) as light yellow solid.

Workup

  1. filtrationAfter filtered through a pad of celite
  2. washwashed with EtOAc
  3. washthe filtrate was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified with mixture of methanol, dichloromethane and ammonia

Sources & evidence

ORD record
ord-c86f8c1d52f543c7885bc674ab237ee0
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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