1,2-Dimethoxyethane → HCID 46830920, compound

HRID 1848344Notes

Reaction equation

I[C:2]1[N:7]2[N:8]=[C:9]([C:11]3([CH2:14][OH:15])[CH2:13][CH2:12]3)[N:10]=[C:6]2[C:5]([O:16][CH3:17])=[CH:4][CH:3]=1.CO[CH2:20][CH2:21]OC>C([O-])([O-])=O.[K+].[K+].[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:15][CH2:14][C:11]1([C:9]2[N:10]=[C:6]3[C:5]([O:16][CH3:17])=[CH:4][CH:3]=[C:2]([C:13]4[CH:12]=[C:11]([CH:14]=[CH:20][CH:21]=4)[C:9]#[N:8])[N:7]3[N:8]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 80 °C

Procedure

[1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropyl]-methanol (compound 308)(0.24 g, 0.07 mmol) was dissolved in DME (4.5 mL) and 1 M K2CO3 (1.4 mL). 5-CN-3-pyridinyl boronic acid (0.21 g, 1.4 mmol) was added followed by Pd(PPh3)4 (0.04 g, 0.035 mmol). The mixture was shaken at 80° C. for 18 h. Brine was added and aqueous phase was extracted with DCM (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using DCM:MeOH 99:1 as eluent. The impure product was suspended in 2-propanol and filtered to provide the title compound as a solid.

Workup

extractionaqueous phase was extracted with DCM (×3)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography on silica
filtrationfiltered

Sources & evidence

ORD record: ord-b2e5ac1523044708b9a72d75b61ae977
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952162B2

Reaction notes

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