Ethyl bromoacetate → HCID 178472607, compound

HRID 713433Notes

Reaction equation

HRID 713433 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:14][NH:15]2)=[CH:11][CH:10]=1.CCN(CC)CC>>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][N:21]1[CH2:20][CH2:19][CH:18]([C:13]2[C:12]3[C:16](=[CH:17][C:9]([F:8])=[CH:10][CH:11]=3)[NH:15][N:14]=2)[CH2:23][CH2:22]1)[CH3:7]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 178505426HCID 178505426, compound

Product 1

HCID 178472607HCID 178472607, compoundYield 33.3%

Conditions

Temperature
85 °C

Procedure

To a suspension of ethyl 2-bromoacetate (0.55 g, 3.3 mmol) and 6-fluoro-3-piperidin-4-yl-1H-indazole (0.60 g, 2.7 mmol in 10 mL of acetonitrile) was added Et3N (1.4 g, 13.7 mmol) and the reaction mixture was stirred at 85° C. for 15 hours. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was redissolved in DCM (50 mL), washed with water, brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography gave the title compound (0.29 g, 0.90 mmol) as a white solid. MS (ESI) m/z 306.9 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.54 min.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was redissolved in DCM (50 mL)
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-85658d98313c4d19a2e465b44e7bd8c3
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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