5-(Tributylstannyl)-1,3-thiazole → 3-Chloro-6-(5-thiazolyl)isoquinoline

HRID 523056Notes

Reaction equation

HRID 523056 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([Cl:12])=[CH:5]2.C([Sn](CCCC)(CCCC)[C:18]1[S:22][CH:21]=[N:20][CH:19]=1)CCC>COCCOC.CO.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>[Cl:12][C:6]1[N:7]=[CH:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([C:18]1[S:22][CH:21]=[N:20][CH:19]=1)=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 27632575-(Tributylstannyl)-1,3-thiazoleHCID 226075306-Bromo-3-chloroisoquinoline

Product 1

HCID 899957463-Chloro-6-(5-thiazolyl)isoquinolineYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86595564Dimethoxyethane methanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 6-bromo-3-chloroisoquinoline (39 mg, 0.16 mmol), 5-(tributylstannyl)-thiazole (72 mg, 0.19 mmol) and Pd(PPh3)4 (18.6 mg, 0.016 mmol) in DME/MeOH (3/1 mL) was stirred at 120° C. under microwave irradiation for 60 minutes. The reaction mixture was filtered and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with 25% EtOAc in cyclohexane to afford the title compound (11 mg, 28%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified
  4. washeluting with 25% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-d6c58911c82f49dea7effa019ccf4c40
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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