Cesium carbonate → Methyl 2-tert-Butyl-4-((2-((tert-butyldimethylsilyloxy)methyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylate

HRID 1772155Notes

Reaction equation

Br[CH2:2][C:3]1[N:4]=[C:5]([C:12]([CH3:15])([CH3:14])[CH3:13])[S:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[Si:16]([O:23][CH2:24][C:25]1[C:30]([B:31]2[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]2)=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:40])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:12]([C:5]1[S:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:3]([CH2:2][NH:40][C:26]2[CH:27]=[CH:28][CH:29]=[C:30]([B:31]3[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:38])([CH3:39])[O:32]3)[C:25]=2[CH2:24][O:23][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[N:4]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension of 125a (1 g, 3.4 mmol), 2-((tert-butyldimethylsilyloxy)methyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (125b) (1.1 g, 3.1 mmol) and cesium carbonate (1.3 g, 4.1 mmol) in acetonitrile (30 mL) was stirred at 45° C. overnight. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was purified on silica gel eluting with 0 to 1% EtOAc in petroleum ether to afford 125c as yellow oil (1.1 g, 56%). LCMS: (M+H)+ 575.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated at reduced pressure
customThe residue was purified on silica gel eluting with 0 to 1% EtOAc in petroleum ether

Sources & evidence

ORD record: ord-5bb0613d9fe24fb79469d0da71d173e1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249123B2

Reaction notes

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