Water → HCID 68497450, compound

HRID 1038768Notes

Reaction equation

HRID 1038768 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][NH:16]3)=[N:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.Br[CH2:30][C:31]([O:33]C(C)(C)C)=[O:32].O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][N:16]3[CH2:30][C:31]([OH:33])=[O:32])=[N:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 68491789HCID 68491789, compound

Product 1

HCID 68497450HCID 68497450, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(2,3-Dihydro-1H-indol-4-yloxy)nicotinic acid ethyl ester (1.13 g, 3.97 mmol) was dissolved in DMF (5 mL). To the solution were added triethylamine (0.665 mL, 4.77 mmol) and tert-butyl bromoacetate (0.704 g, 4.77 mmol), and the resulting solution was stirred for 16 hours at room temperature, followed by stirring for 4 hours at 50° C. Water (100 mL) was added and the resulting solution was extracted with ethyl acetate (100 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated to give a pale brown oil (1.58 g). This oil was dissolved in trifluoroacetic acid (10 mL) and the solution was stirred for 1 hour at room temperature. The solution was concentrated, and the pH of the solution was adjusted to 5 using saturated sodium bicarbonate solution. The resulting solution was extracted with a mixture of ethyl acetate (50 mL)-THF (25 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was recrystallized from a mixed solution of ethyl acetate and n-hexane to yield 0.220 g of the title compound as a pale brown powder.

Workup

  1. stirringby stirring for 4 hours at 50° C
  2. extractionthe resulting solution was extracted with ethyl acetate (100 mL)
  3. washAfter the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2f5338cea42840a3a01de2a56b53cd25
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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