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

HRID 1715694
Notes
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Reaction equation

HRID 1715694 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 10968526(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol esterHCID 574467974-{[4-(4-Bromophenyl)pyrimidin-2-yl]amino}benzenesulfonamide

Product 1

HCID 114946764-[(4-{4-[(1E)-3-hydroxyprop-1-en-1-yl]phenyl}pyrimidin-2-yl)amino]benzenesulfonamide
Yield 30.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

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

  1. temperatureThe reaction mixture is cooled to room temperature
  2. stirringThe reaction mixture is then stirred for 16 h at room temperature
  3. concentrationThe reaction mixture is concentrated
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes