Sodium Carbonate → HCID 44176975, compound

HRID 2090162Notes

Reaction equation

HRID 2090162 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[N:18]1[CH:23]=[CH:22][C:21]([C:13]2[N:12]=[C:11]([NH:10][C:8]3[CH:7]=[CH:6][C:5]4[S:1][CH:2]=[N:3][C:4]=4[CH:9]=3)[CH:16]=[N:15][CH:14]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86652757HCID 86652757, compound

Product 1

HCID 44176975HCID 44176975, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of benzothiazol-5-yl-(6-chloro-pyrazin-2-yl)-amine (0.06 g, 0.228 mmol), pyridine-4-boronic acid (0.043 g, 0.342 mmol), sodium carbonate (0.124 g, 1.14 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.013 g, 0.0114 mmol) in DME:water (3:2, 5 mL) was heated at reflux for 22 h. The reaction mixture was concentrated under reduced pressure and the residue obtained was extracted with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (5% methanol in CH2Cl2 as eluent) to yield N-(6-pyridin-4-ylpyrazin-2-yl)-1,3-benzothiazol-5-amine (0.035 g, 50%) as a yellow solid. 1H NMR (CD3OD) δ 9.31 (s, 1H), 8.98 (d, J=2.02 Hz, 1H), 8.75-8.74 (d, J=5.31 Hz, 2H), 8.64 (s, 1H), 8.31 (s, 1H), 8.24-8.22 (d, J=5.99 Hz, 2H), 8.06-8.04 (d, J=8.77 Hz, 1H), 7.74-7.71 (dd, J=10.73, 2.01 Hz, 1H); MS (API-ES/Positive); m/z: 306 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue obtained
  5. extractionwas extracted with dichloromethane
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-7c9232eafbe04377b2f6c6198c9a1b90
Source dataset
uspto-grants-2013_05
Patent number
US08436171B2

Reaction notes

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