Sodium Carbonate → 3-Methyl-6-pyridin-3-yl-3H-benzothiazol-2-one

HRID 1623561Notes

Reaction equation

HRID 1623561 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH3:10])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:10][N:6]1[C:5]2[CH:11]=[CH:12][C:2]([C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)=[CH:3][C:4]=2[S:8][C:7]1=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 42065626-Bromo-3-methylbenzo[d]thiazol-2(3H)-one

Product 1

HCID 498197323-Methyl-6-pyridin-3-yl-3H-benzothiazol-2-oneYield 131%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 6-Bromo-3-methyl-3H-benzothiazol-2-one (200 mg, 0.82 mmol), 3-pyridyl boronic acid (78 mg, 0.63 mmol), polymer-supported Pd(PPh3)4 (0.11 mmol/g, 115 mg, 0.0126 mmol) and Na2CO3 (2 M in water, 0.65 mL, 1.3 mmol) in DME (7 mL) was heated to reflux for overnight. After filtration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-4%) and yielded the title compound (200 mg). MS (ESI) m/z 243.0 (M+H, 1H NMR (400 MHz, CD2Cl2) δ ppm 3.52 (s, 3H), 7.23 (d, J=8.4 Hz, 1H), 7.43-7.46 (m, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.73 (s, 1H), 7.93-7.96 (m, 1H), 8.62 (m, 1H), 8.88 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-4%)

Sources & evidence

ORD record
ord-0ad9fda4572040398e62253f5702fc1c
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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