Triethylamine → ethyl 2-[1-[4-(4-cyanobenzamido)benzyl]-1H-indazol-3-yl]acetate

HRID 589395Notes

Reaction equation

HRID 589395 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)#[N:32].C(=O)(O)[O-].[Na+]>ClCCl>[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:8]3)=[CH:22][CH:23]=2)=[O:38])=[CH:35][CH:34]=1)#[N:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 89590263ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate

Product 1

HCID 90449130ethyl 2-[1-[4-(4-cyanobenzamido)benzyl]-1H-indazol-3-yl]acetateYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate (176 mg, 0.569 mmol) and triethylamine (173 mg, 1.71 mmol) were dissolved in dichloromethane (15 mL), and in an ice bath dichloromethane solution (10 mL) of 4-cyanobenzoyl chloride (95 mg, 0.574 mmol) was added dropwise slowly. Upon completion of the dropwise addition, it was reacted at room temperature for 16 hours. An aqueous solution of sodium bicarbonate was added to quench, and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduce pressure, chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a white solid 121 mg, at a yield of 48.5%.

Workup

  1. additionUpon completion of the dropwise addition, it
  2. customwas reacted at room temperature for 16 hours
  3. customto quench
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e4b14be0077849baafcc421a9c9352a4
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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