HCID 22238484, compound → HCID 22238489, compound

HRID 1743136Notes

Reaction equation

HRID 1743136 reaction equation
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5]([C:9]2[O:13][CH:12]=[N:11][CH:10]=2)=[C:4]([O:14][CH3:15])[CH:3]=1.[C:16]([C:18]1[N:19]=[CH:20][S:21][CH:22]=1)#[CH:17]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:15][O:14][C:4]1[CH:3]=[C:2]2[C:7]([CH:17]=[C:16]([C:18]3[N:19]=[CH:20][S:21][CH:22]=3)[NH:1]2)=[CH:6][C:5]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1

Participants

5

Reactant 2

HCID 22238484HCID 22238484, compoundHCID 222384914-Ethynyl-1,3-thiazole

Product 1

HCID 22238489HCID 22238489, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(4-amino-5-iodo-2-methoxyphenyl)oxazole (WO 0181340) (0.293 g, 0.93 mmol) in diethylamine (2.5 mL) was added 4-ethynylthiazole (0.118 g, 1.08 mmol) and bis(triphenylphosphine)palladiumdichloride (0.019 g, 0.027 mmol). The contents were purged with nitrogen and heated in a steel bomb at 120° C. for 20 minutes. The reaction mixture was cooled to rt and purified by silica gel column chromatography to provide the title compound (0.065 g, 20%). HPLC Ret. t=2.79 min. (A); LC/MS M+1=298.27.

Workup

  1. customThe contents were purged with nitrogen
  2. temperatureThe reaction mixture was cooled to rt
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-216e78e1879e4426a2b23271b7c13bde
Source dataset
uspto-grants-2006_03
Patent number
US07008958B2

Reaction notes

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