Dichloromethane → 5-pyridin-3-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 1678251Notes

Reaction equation

ClCCl.I[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:9]=[CH:8]2.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:9]=[CH:8]3)[CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

[1,1′-Bis(diphenylphosphino)-ferrocene)dichloropalladium(II) 1:1 complex with dichloromethane (204 mg, 0.25 mmol) was added to a mixture of 5-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (Preparation #17a, 1.87 g, 5.00 mmol), pyridine-3-boronic acid (737 mg, 6.00 mmol), and Cs2CO3 (4.89 g, 15.0 mmol) in 1,2-dimethoxy-ethane (16 mL) and water (3.2 mL) under a nitrogen atmosphere. The reaction was heated at about 100° C. overnight, cooled, concentrated and extracted with CH2Cl2 (about 30 mL). The extracts were adsorbed onto silica and purified over a silica gel column eluting first with heptane:EtOAc (85:15) and then with heptane:EtOAc (3:2) to yield 5-pyridin-3-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (857 mg, 53%) as an oil. RP HPLC (Table 1, Method e) Rt=3.04, m/z: (MH)+ 326.

Workup

temperaturecooled
concentrationconcentrated
extractionextracted with CH2Cl2 (about 30 mL)
custompurified over a silica gel column
washeluting first with heptane:EtOAc (85:15)

Sources & evidence

ORD record: ord-ddc63245521b48529b8b959a51f485e6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008481B2

Reaction notes

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