Ethylacetate methanol → HCID 59424545, compound

HRID 1710932Notes

Reaction equation

HRID 1710932 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](CCCC)(CCCC)CCCC)[S:10][C:3]=12.Br[C:25]1[CH:37]=[CH:36][C:28]([CH2:29][N:30]2[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31]2)=[CH:27][CH:26]=1.CO.CCOC(C)=O>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:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:25]3[CH:37]=[CH:36][C:28]([CH2:29][N:30]4[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31]4)=[CH:27][CH:26]=3)[S:10][C:3]=12

Participants

6

Reactant 3

HCID 21584119Ethylacetate methanolHCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridineHCID 59424626HCID 59424626, compound

Product 1

HCID 59424545HCID 59424545, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 98 (2.44 g, 5.30 mmol) and bromide 97 (1.3 g, 5.07 mmol) in dry toluene (30 mL) was added Pd(PPh3)4 (290 mg, 0.25 mmol). The reaction mixture was heated to reflux for 1.5 h, cooled to room temperature and the solvent was removed under reduced pressure. The resultant solid was purified by column chromatography, eluents EtOAc-Hexane (1:1) then MeOH/EtOAc (20:80), to afford title compound 99 (1.24 g, 71% yield) as a white solid. MS (m/z): 345.1/347.1 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 h
  3. customthe solvent was removed under reduced pressure
  4. customThe resultant solid was purified by column chromatography, eluents EtOAc-Hexane (1:1)

Sources & evidence

ORD record
ord-f7e86a6292fb4067bd8dcf4c7c670bca
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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