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Potassium Phosphate, Tribasic → HCID 59392849, compound

HRID 216732
Notes
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Reaction equation

HRID 216732 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[N:7]2.[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[CH:28]=[CH:27][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][C:24]=2[CH3:38])=[O:22])[CH2:17][CH2:16]1)[CH3:14].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:26]1[CH:27]=[CH:28][C:23]([C:21]([N:18]3[CH2:19][CH2:20][N:15]([CH2:13][CH3:14])[CH2:16][CH2:17]3)=[O:22])=[C:24]([CH3:38])[CH:25]=1)[CH:8]=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 593926708-Bromo-2-chloroquinoxalineHCID 59392740HCID 59392740, compound

Product 1

HCID 59392849HCID 59392849, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
105 °C

Procedure

A microwave tube is charged with 8-Bromo-2-chloro-quinoxaline (Step 1.4, 298 mg, 1.226 mmol), (4-Ethyl-piperazin-1-yl)-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone (439 mg, 1.226 mmol), K3PO4 (532 mg, 2.450 mmol) and Pd(PPh3)4 (43.8 mg, 0.0368 mmol). After several cycles of vacuum/purge with argon, 5 ml of dry DMA are added. The reaction mixture is then heated to 105° C. for 4 h. After cooling, the suspension is poured onto 70 ml de-ionized water and filtered. The cake is re-taken in EtOAc, washed with saturated brine and dried over Na2SO4. After filtration, the mixture is concentrated in vacuo. The residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 from 1:0=>0:1) to afford the title compound as a pale brown foam, Rt=0.833 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 439 (M+1, 79Br)+.

Workup

  1. customAfter several cycles of vacuum/purge with argon, 5 ml of dry DMA
  2. additionare added
  3. temperatureAfter cooling
  4. additionthe suspension is poured onto 70 ml de-ionized water
  5. filtrationfiltered
  6. washwashed with saturated brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. concentrationthe mixture is concentrated in vacuo
  10. customThe residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 from 1:0=>0:1)

Sources & evidence

ORD record
ord-173a341e7dae4de0a74121e0b62f96e1
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193189B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes