6-Bromo-2-(methylsulfanyl)-1,3-benzothiazole → HCID 58529564, compound

HRID 1972982Notes

Reaction equation

HRID 1972982 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7](SC)[S:8][C:4]=2[CH:3]=1.[Br-].[CH2:14]([Zn+])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>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.CCOC(C)=O>[CH2:14]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([Br:1])[CH:12]=[CH:11][C:5]=2[N:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 179535146-Bromo-2-(methylsulfanyl)-1,3-benzothiazoleHCID 178419772HCID 178419772, compound

Product 1

HCID 58529564HCID 58529564, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A degassed mixture of 6-bromo-2-(methylthio)-1,3-benzothiazole (4.20 g, 16.14 mmol), tetrakis(triphenylphosphine)palladium(0) (186 mg, 0.161 mmol) and benzylzinc bromide (0.5 M in THF, 61.34 mL) was heated at 60° C. for 4 hrs. EtOAc (200 mL) was added and the organic layer was washed with saturated, aqueous NaHCO3 (3×150 mL), then water (3×150 mL). The organic layer was dried over MgSO4 and concentrated. The crude material was purified by ISCO® chromatography using 4% EtOAc in hexane to obtain the desired product (1.50 g, 28%). 1H NMR (400 MHz, acetone-d6) δ 8.20 (s, 1H), 7.88 (d, 1H), 7.62 (d, 1H), 7.44-7.30 (m, 5H), 4.44 (s, 2H); LC-MS m/z [M+H]+ 304.2 & 306.1, RT 4.02 min.

Workup

  1. washthe organic layer was washed with saturated, aqueous NaHCO3 (3×150 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record
ord-4fa96f02d4174bdfab06bae037068e36
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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