Triethylamine → HCID 66856518, compound

HRID 1191323Notes

Reaction equation

HRID 1191323 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[C:18](O)=[O:19].ClC(OCC(C)C)=O.C(N(CC)CC)C.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C.CO>[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]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 66849096HCID 66849096, compound

Product 1

HCID 66856518HCID 66856518, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 6-bromo-2-oxo-3-(thiophene-2-yl)-1,2-dihydroquinoline-4-carboxylic acid (1.00 g, 2.86 mmol) in tetrahydrofuran (11.4 ml) were added isobutyl chloroformate (0.364 ml, 2.86 mmol) and triethylamine (0.398 ml, 2.86 mmol) at 0° C. The reaction was allowed to stir at room temperature for 30 min. The reaction was then filtered to remove solids and placed in an ice bath at 0° C. Sodium borohydride (0.119 g, 3.14 mmol) was added to the reaction mixture followed by methanol (3 ml). This mixture was allowed to warm to room temperature and stirred for 4 h. The reaction was diluted in ethyl acetate (50 ml) and extracted with 1 N sodium hydroxide (3×40 ml) and sodium chloride (1×40 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated to afford 6-bromo-4-(hydroxymethyl)-3-(thiophen-2-yl)quinolin-2(1H)-one as a crude, yellow oil. Compound used without further purification. LCMS (M+H)=337.7.

Workup

  1. filtrationThe reaction was then filtered
  2. customto remove solids
  3. customplaced in an ice bath at 0° C
  4. temperatureto warm to room temperature
  5. stirringstirred for 4 h
  6. extractionextracted with 1 N sodium hydroxide (3×40 ml) and sodium chloride (1×40 ml)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb740f2a50b42fba7765af0b658b242
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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