2-(Tributylstannyl)-1,3-thiazole → HCID 59626021, compound

HRID 401631Notes

Reaction equation

HRID 401631 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([Sn](CCCC)(CCCC)[C:21]1[S:22][CH:23]=[CH:24][N:25]=1)CCC>O1CCOCC1.C(Cl)Cl.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>[S:22]1[CH:23]=[CH:24][N:25]=[C:21]1[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 12067225Ethyl 2-bromo-6-benzothiazolecarboxylate

Product 1

HCID 59626021HCID 59626021, compoundYield 84.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 2-bromo-benzothiazole-6-carboxylate 1w (150 mg, 0.53 mmol), 2-tributylstannylthiazole 9p (0.25 mL, 0.79 mmol), and Pd(PPh3)4 (30 mg, 0.03 mmol) in dioxane (2 mL) was heated at 130° C. for 30 min under microwave. The reaction mixture was diluted with CH2Cl2, washed with aq. NaHCO3, dried over Na2SO4, and concentrated. Purification by flash column chromatography (silica gel, 10% EtOAc/heptane) gave 9q (130 mg).

Workup

  1. washwashed with aq. NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (silica gel, 10% EtOAc/heptane)

Sources & evidence

ORD record
ord-f4ff35d68563447f93e07cbcb4e7905f
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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