Sodium Carbonate → 6-(5-(Methylthio)-1,3,4-thiadiazol-2-yl)isoquinoline

HRID 2075364Notes

Reaction equation

HRID 2075364 reaction equation
Br[C:2]1[S:3][C:4]([S:7][CH3:8])=[N:5][N:6]=1.[CH:9]1[C:18]2[C:13](=[CH:14][C:15](B(O)O)=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[CH3:8][S:7][C:4]1[S:3][C:2]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[CH:9]=[N:10][CH:11]=[CH:12]3)=[N:6][N:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 222696212-Bromo-5-(methylsulfanyl)-1,3,4-thiadiazoleHCID 44119669(Isoquinolin-6-yl)boronic acid

Product 1

HCID 579918536-(5-(Methylthio)-1,3,4-thiadiazol-2-yl)isoquinolineYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 25 mL round bottom flask was added 2-bromo-5-(methylthio)-1,3,4-thiadiazole (0.40 g, 1.9 mmol) (prepared as described in WO 97/30981, isoquinolin-6-ylboronic acid (0.39 g, 2.3 mmol) (prepared as described in US Patent Publication No. US 2007/0173506), Pd(PPh3)4 (0.11 g, 0.095 mmol), 2.4 mL of a 2 M Na2CO3 aqueous solution and 2 mL of DME. The reaction was heated at reflux for 16 hours. The reaction mixture was concentrated, and the residue was purified by column chromatography on silica gel (eluting with a gradient from 0 to 70% EtOAc in hexanes) to provide 6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)isoquinoline (0.29 g, 59%) as a yellow solid. LCMS (M+H) 260 calc. for C12H10N3S2 260.0.

Workup

  1. customprepared
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 16 hours
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was purified by column chromatography on silica gel (
  6. washeluting with a gradient from 0 to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b7cc061bbd72486096460119576935b8
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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