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Cesium carbonate → HCID 67520373, compound

HRID 1926365
Notes
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Reaction equation

HRID 1926365 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:17])=[N:12][CH:13]=[C:14](Br)[CH:15]=1.[C:18]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O:20][CH3:21])=[O:19].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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>[CH3:21][O:20][C:18](=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([C:14]2[CH:13]=[N:12][C:11]([NH2:17])=[C:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH:15]=2)[CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 67389127HCID 67389127, compound

Product 1

HCID 67520373HCID 67520373, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 21886435
1,4-Dioxane--water (1/1)
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (1.37 g, 4.5 mmol), 3-(carbomethoxy)phenylboronic acid (0.85 g, 4.7 mmol), Pd(PPh3)4 (5 mol %), and Cs2CO3 (3.5 g, 10.8 mmol) in dioxane/H2O (4:1, 30 mL) were heated under nitrogen at 90° C. for 5 h. Solvents were removed in vacuo, water (10 mL) was added to the residue, and the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material thus obtained was purified by column chromatography on silica gel using mixtures of EtOAc/Hexanes to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=7.28 (brs, 2H), 7.41 (t, J=6.9 Hz, 1H), 7.51 (t, J=6.9 Hz, 1H), 7.64 (d, J=7.5 Hz, 1H), 7.77 (d, J=6.3 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 8.01-8.05 (m, 2H), 8.18 (d, J=2.1 Hz, 1H), 8.26 (t, J=1.8 Hz, 1H), 8.47 (d, J=2.1 Hz, 1H).

Workup

  1. customSolvents were removed in vacuo, water (10 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material thus obtained
  8. customwas purified by column chromatography on silica gel using mixtures of EtOAc/Hexanes

Sources & evidence

ORD record
ord-6232aea414a84c71976901e646854117
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178668B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes