Potassium Fluoride → HCID 86687694, compound

HRID 1473625Notes

Reaction equation

HRID 1473625 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)CCC.[Br:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][C:21]=1[O:27][CH3:28].[F-].[K+]>O1CCOCC1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)=[CH:22][C:21]=1[O:27][CH3:28]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 121872021-Bromo-4-iodo-2-methoxybenzene

Product 1

HCID 86687694HCID 86687694, compoundYield 71.7%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.391 g, 0.479 mmol), 2-tributylstannylthiazole (3.01 ml, 9.59 mmol), 1-bromo-4-iodo-2-methoxybenzene (3.00 g, 9.59 mmol), and potassium fluoride (1.499 g, 38.3 mmol) in 10 mL dioxane was heated to 100° C. overnight. LC/MS showed mostly product, so the reaction mixture was diluted with DCM and washed with water. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography (0-100% EtOAc/heptane) gave 2-(4-bromo-3-methoxyphenyl)thiazole (1.858 g, 6.88 mmol, 71.7% yield). (M+H)+=271.2.

Workup

  1. washwashed with water
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-d39900e670ca4891a56bff28481da953
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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