2-Propanol, sodium salt (1:1) → 5-(2-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-isopropoxy-benzonitrile

HRID 1891495Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Prepared using General Procedure 2. To a solution of 5-(2-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-fluorobenzonitrile (0.043 g, 0.095 mmol) in isopropanol (2 mL) was added sodium isopropoxide (0.07 g, 0.090 mmol). The reaction mixture was heated at 60° C. for 12 h. Upon cooling, the solvent was removed under a stream of N2 and the crude reaction mixture was carried onto the next step without further purification. LCMS-ESI (m/z) calculated for C28H34N2O2SSi: 490.7, tR=5.06 min (Method 3).

Workup

customPrepared
temperatureUpon cooling
customthe solvent was removed under a stream of N2
customthe crude reaction mixture
customwas carried onto the next step without further purification

Sources & evidence

ORD record: ord-13d71d3add654541814b14da64604921
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507538B2

Reaction notes

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