Hexane → HCID 86636115, compound

HRID 1047440Notes

Reaction equation

HRID 1047440 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6]N=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[CH3:11]CCCCC.[Li]CCCC.Br[C:23]1[N:28]=[C:27]([CH2:29][N:30]([CH2:38][CH2:39][O:40][CH3:41])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:26]=[CH:25][CH:24]=1>C1COCC1.[Cl-].[Cl-].[Zn+2].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.CCOCC>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:23]3[N:28]=[C:27]([CH2:29][N:30]([CH2:38][CH2:39][O:40][CH3:41])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:26]=[CH:25][CH:24]=3)=[CH:8][C:4]=2[CH:11]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 8058HexaneHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 57967257HCID 57967257, compoundHCID 178418339Butyllithium

Product 1

HCID 86636115HCID 86636115, compoundYield 50%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-chlorothieno[3,2-b]pyridine (6) (4.49 g, 26.6 mmol) in THF (20 ml) was treated with 2.5 M hexane solution of n-BuLi (11.1 mL, 27.9 mmol) at −78° C. and allowed to stir at the same temperature for 45 min. The reaction mixture was then treated with 1M ether solution of ZnCl2 (28 mL, 28 mmol) and stirred at room temperature for an additional 1 h. The reaction mixture was then treated with 56 (2.3 g, 6.7 mmol) and Pd(PPh3)4 and was heated to reflux for 2 hrs. It was quenched with saturated NaHCO3 (50 mL) and extracted with EtOAc (2×50 mL). The extract was dried over anhydrous Na2SO4, filtered and evaporated. Obtained crude product was purified by flash chromatography (using the gradient 60-80% EtOAc/hexanes as an eluent), yielding 57 (1.43 g, 50% yield). MS (m/z): 434.2 (M+1).

Workup

  1. stirringstirred at room temperature for an additional 1 h
  2. temperaturewas heated
  3. temperatureto reflux for 2 hrs
  4. customIt was quenched with saturated NaHCO3 (50 mL)
  5. extractionextracted with EtOAc (2×50 mL)
  6. dry with materialThe extract was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customObtained crude product
  10. customwas purified by flash chromatography (

Sources & evidence

ORD record
ord-ebe501ed109945038e065df8230922e4
Source dataset
uspto-grants-2013_10
Patent number
US08569503B2

Reaction notes

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