7-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine → HCID 58474635, compound

HRID 1400861Notes

Reaction equation

HRID 1400861 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][O:11][C:10]2=[O:15])=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([Sn](CCCC)(CCCC)CCCC)[S:25][C:18]=12>C1(C)C=CC=CC=1.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:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:2]3[N:7]=[CH:6][C:5]([CH2:8][N:9]4[CH2:14][CH2:13][CH2:12][O:11][C:10]4=[O:15])=[CH:4][CH:3]=3)[S:25][C:18]=12

Participants

5

Reactant 2

HCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridineHCID 58474481HCID 58474481, compound

Product 1

HCID 58474635HCID 58474635, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 197 (373 mg, 1.376 mmol) in toluene (10 mL) was added the 7-chloro-2-(tributylstannyl)thieno[3,2-b]pyridine 198 (631 mg, 1.376 mmol) and Pd(PPh3)4 (159 mg, 0.138 mmol). The reaction mixture was heated to reflux for 24 hours. The reaction mixture was then cooled to RT and concentrated. The residue was triturated with Et2O to afford the title compound 199 (363 mg, 73% yield) as beige solid. MS: 360 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated
  4. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-6626f45057c8456c99545eef386c5cff
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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