Triethylamine → HCID 123850371, compound

HRID 733106Notes

Reaction equation

HRID 733106 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:23])([CH3:22])[C:7](=[O:21])[N:8]2[C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:36]([O:35][C:33](=[O:34])[CH2:32][N:18]1[CH2:19][CH2:20][CH:15]([CH2:14][NH:13][C:11]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=3)[C:6]([CH3:23])([CH3:22])[C:7]2=[O:21])=[O:12])[CH2:16][CH2:17]1)([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 79177tert-Butyl bromoacetate2×HCID 516892Sodium BicarbonateHCID 67231993HCID 67231993, compound

Product 1

HCID 123850371HCID 123850371, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 6-fluoro-3,3-dimethyl-2-oxo-N-(piperidin-4-ylmethyl)indoline-1-carboxamide (200 mg, 0.63 mmol, step 2 in Example 17) and triethylamine (114 μL, 0.82 mmol) in tetrahydrofuran (3 mL) was stirred at 0° C., it was slowly added tert-butyl bromoacetate (111 μL, 0.75 mmol). The reaction mixture was stirred at room temperature for 5 h and at 35° C. for 4 h. It was further added triethylamine (17 μL, 0.12 mmol) and tert-butyl bromoacetate (18 μL, 0.12 mmol). The solution was stirred at room temperature overnight. The resulting solution was added sat. sodium bicarbonate. It was extracted with ethyl acetate (10 mL×3). The organic phase was washed with brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a column of aminopropyl-silica gel eluting with ethyl acetate/hexane (1:10 to 1:6) to give 203 mg (74%) of the titled compound.

Workup

  1. stirringThe solution was stirred at room temperature overnight
  2. extractionIt was extracted with ethyl acetate (10 mL×3)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a column of aminopropyl-silica gel eluting with ethyl acetate/hexane (1:10 to 1:6)

Sources & evidence

ORD record
ord-86029688d91e47d9ae42edd2b66b4ece
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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