Tetrahydrofuran → HCID 86079793, compound

HRID 1162590Notes

Reaction equation

HRID 1162590 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][C:16](=O)[CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B#B.C1COCC1.C([O-])(O)=O.[Na+]>>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([NH:15][CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 6328200DiboronHCID 30515126HCID 30515126, compound

Product 1

HCID 86079793HCID 86079793, compoundYield 39.7%

Procedure

To N-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-2-thiophen-2-yl-acetamide (270 mg, 0.79 mmol) was added diborane in THF (1.6 mL, 1M solution, 1.58 mmol). The mixture was stirred at room temperature for 2 h. Saturated NaHCO3 solution was added, and the mixture was extracted into ethyl acetate (3×5 mL). Combined ethyl acetate extracts were dried over Na2SO4, concentrated and purified on silica gel column to afford [4-(4-isopropyl-phenyl)-thiazol-2-yl]-(2-thiophen-2-yl-ethyl)-amine (103 mg). LCMS m/z: 330 (M+1)+.

Workup

  1. extractionthe mixture was extracted into ethyl acetate (3×5 mL)
  2. dry with materialCombined ethyl acetate extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel column

Sources & evidence

ORD record
ord-cee8bf507d7b47868b4c1c55a2f2a415
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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