1,4-Dioxane → HCID 59164432, compound

HRID 1894076Notes

Reaction equation

HRID 1894076 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](I)[C:7]([CH:11]([CH3:13])[CH3:12])=[CH:6][C:5]=1[NH2:14].[CH3:16][N:17]1[C:21]([Sn](CCCC)(CCCC)CCCC)=[CH:20][CH:19]=[N:18]1.O1CCOCC1>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:21]2[N:17]([CH3:16])[N:18]=[CH:19][CH:20]=2)[C:7]([CH:11]([CH3:13])[CH3:12])=[CH:6][C:5]=1[NH2:14]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 218674551-Methyl-5-(tributylstannyl)-1H-pyrazoleHCID 29928205Methyl 2-amino-5-iodo-4-(propan-2-yl)benzoate

Product 1

HCID 59164432HCID 59164432, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-5-iodo-4-isopropyl-benzoic acid methyl ester (300 mg, 0.94 mmol) and 1-methyl-5-tributylstannanyl-1H-pyrazole (523 mg, 1.5 equiv) were weighed in air and added in a flame-dried flask. [Bistriphenylphosphine]dichloropalladium (67.3 mg, 0.1 equiv) was added and the flask was closed by a septum. Dioxane (1 mL) was added and the mixture was stirred for 18 h (TLC control) at 100° C. The mixture was dissolved with EtOAc, filtered and evaporated to dryness. The crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6)) to yield 2-amino-4-isopropyl-5-(2-methyl-2H-pyrazol-3-yl)-benzoic acid methyl ester (169 mg, 66%) as a yellow solid. (ESI-MS: m/z 274 [M+H]+, rt 5.20 min).

Workup

  1. additionadded in a flame-dried flask
  2. customthe flask was closed by a septum
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6))

Sources & evidence

ORD record
ord-672ed2738d8444428636d29dd744bb96
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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