Sodium Carbonate → HCID 44176974, compound

HRID 2090160Notes

Reaction equation

HRID 2090160 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][NH:15]3)=[CH:11][CH:10]=2)[CH:5]=[N:4][CH:3]=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:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:17]=[C:16]4[C:12]([CH:13]=[CH:14][NH:15]4)=[CH:11][CH:10]=3)[CH:5]=[N:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86652755HCID 86652755, compound

Product 1

HCID 44176974HCID 44176974, compoundYield 36.5%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of (6-chloro-pyrazin-2-yl)-(1H-indol-6-yl)-amine (0.070 g, 0.2868 mmol), pyridine-4-boronic acid (0.042 g, 0.344 mmol), sodium carbonate (0.150 g, 1.43 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0165 g, 0.0143 mmol) in DME:water (3:2, 5 mL) was heated at reflux for 20 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)-1H-indol-6-amine (0.030 g, 36.5%) as a yellow solid. 1H NMR (CD3OD) δ 8.73-8.72 (d, J=5.68 Hz, 2H), 8.51 (s, 1H), 8.23-8.20 (m, 4H), 7.56-7.54 (d, J=8.46 Hz, 1H), 7.22 (d, J=2.99 Hz, 1H), 7.14 (dd, J=10.18, 1.74 Hz, 1H), 6.45 (d, J=2.75 Hz, 1H); MS (API-ES/Positive); m/z: 288 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 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-da2aad9f9d3646608a142f90abe31600
Source dataset
uspto-grants-2013_05
Patent number
US08436171B2

Reaction notes

Loading…