Cesium carbonate → HCID 89963269, compound

HRID 1052290Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1.Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Si:26]([O:25][CH2:24][CH2:23][N:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:11]=[CH:10][C:9]([B:4]3[O:3][C:2]([CH3:21])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:14][CH:13]=2)[CH2:20][CH2:19]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (0.1 g, 0.5 mmol, from Boron Molecular), (2-bromoethoxy)(tert-butyl)dimethylsilane (0.18 g, 0.75 mmol) and cesium carbonate (0.32 g, 1.0 mmol) in acetonitrile (2.0 mL) was stirred at 40° C. overnight. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford the desired product (0.2 g, 88%). LCMS calculated for C24H44BN2O3Si (M+H)+: m/z=447.3. Found 447.3.

Workup

customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%)

Sources & evidence

ORD record: ord-7d8be91559a54aabb327da8e950ced41
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388185B2

Reaction notes

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