Cesium carbonate → HCID 178504229, compound

HRID 2209093Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[N:19][N:20]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:21]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.ICCC.CCOC(C)=O>[CH3:27][Si:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][O:23][CH2:22][N:20]1[CH:21]=[C:17]([C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=2)[CH:18]=[N:19]1

Participants

Conditions

Temperature: 90 °C

Procedure

To solution of 2-bromopyridin-4-ol (0.4 g, 2 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (0.99 g, 3 mmol) in Dioxane/H2O (3 ml/1.5 ml) was added PEPSI-IPr catalyst (0.078 g, 0.115 mmol) and followed by the addition of Cs2CO3 (1.65 g, 5 mmol). The reaction mixture was stirred at 90° C. for 30 minutes. The reaction mixture was diluted with EtOAc and washed with HCl (1N). Two phases were separated and the aqueous phase was extracted with EtOAc (3×). Organic phase were combined and concentrated down under vacuo. The residue was purified by silicone gel column. And 2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyridin-4-ol was obtained (0.61 g, 91.1%). LCMS-ESI+ (m/z): [M+H]+ calcd. for C26H30N5O3: 292.42; found: 292.11.

Workup

washwashed with HCl (1N)
customTwo phases were separated
extractionthe aqueous phase was extracted with EtOAc (3×)
concentrationconcentrated down under vacuo
customThe residue was purified by silicone gel column

Sources & evidence

ORD record: ord-7836c2c67a4a49a4b143a34310ed3d4c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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