Tempo → HCID 77231106, compound

HRID 1191324Notes

Reaction equation

HRID 1191324 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[C:5]2[CH2:18][OH:19].C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C.CC1(C)N([O])C(C)(C)CCC1>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[C:5]2[CH:18]=[O:19]

Participants

6

Reactant 3

HCID 2724126TempoHCID 21865429Bis(acetoxy)iodobenzeneHCID 66856518HCID 66856518, compound

Product 1

HCID 77231106HCID 77231106, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromo-4-(hydroxymethyl)-3-(thiophen-2-yl)quinolin-2(1H)-one (0.155 g, 0.461 mmol) in acetonitrile (4.60 ml) were added bisacetoxy iodobenzene (0.134 g, 0.415 mmol) and 2,2,6,6-tetramethyl piperidin-1-oxyl (7.30 mg, 0.046 mmol). The reaction was allowed to stir at room temperature for 16 h. The reaction was diluted with ethyl acetate (30 ml) and extracted with saturated sodium thiosulfate (1×25 ml), sodium bicarbonate (1×25 ml) and sodium chloride (1×25 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated. Purification of the crude oil by silica chromatography gave 6-bromo-2-oxo-3-(thiophen-2-yl)-1,2-dihydroquinoline-4-carbaldehyde as a white solid. LCMS (M+H)=335.76.

Workup

  1. extractionextracted with saturated sodium thiosulfate (1×25 ml), sodium bicarbonate (1×25 ml) and sodium chloride (1×25 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude oil by silica chromatography

Sources & evidence

ORD record
ord-f70e539162a545d98d8dccc362280083
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

Loading…