Trifluoroacetic acid → 4-[(4-{4-[(1E)-3-hydroxyprop-1-en-1-yl]phenyl}pyrimidin-2-yl)amino]benzenesulfonamide

HRID 1715694Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.C([Si](C)(C)[O:30][CH2:31]/[CH:32]=[CH:33]/B1OC(C)(C)C(C)(C)O1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.O.C(O)C>[OH:30][CH2:31]/[CH:32]=[CH:33]/[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A flask is charged with 4-{[4-(4-bromophenyl)pyrimidin-2-yl]amino}benzenesulfonamide (0.681 g, 1.68 mmol), tert-butyl(dimethyl){[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane (1.00 g, 3.35 mmol), (Ph3)4Pd (0.194 g, 0.168 mmol), potassium carbonate (0.695 g, 5.03 mmol), ethanol (3.0 ml), water (3.0 ml), and toluene (25 ml). The reaction mixture is stirred at 85° C. for 4 h. The reaction mixture is cooled to room temperature, and trifluoroacetic acid (1.0 ml) is added. The reaction mixture is then stirred for 16 h at room temperature. The reaction mixture is concentrated and purified on preparative HPLC to yield 0.196 g of a yellow solid. MS (ESI) m/z 383.2; HRMS: calcd for C19H18N4O3S+H+, 383.11724; found (ESI-FTMS, [M+H]1+), 383.11752.

Workup

temperatureThe reaction mixture is cooled to room temperature
stirringThe reaction mixture is then stirred for 16 h at room temperature
concentrationThe reaction mixture is concentrated
custompurified on preparative HPLC

Sources & evidence

ORD record: ord-2b9f74d9422d40adb5ebc5ed4079b739
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799915B2

Reaction notes

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