Diethyl Ether → HCID 178437401, compound

HRID 926498Notes

Reaction equation

HRID 926498 reaction equation
[N:1]1([C:6]2[CH:21]=[CH:20][C:9]([CH2:10][CH:11]([C:16](=O)[CH2:17][CH3:18])[C:12]([O:14]C)=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][C:11]3[C:16]([CH2:17][CH3:18])=[N:27][C:26]4[C:28]([C:12]=3[OH:14])=[CH:29][C:23]([Br:22])=[CH:24][CH:25]=4)=[CH:20][CH:21]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 78074-BromoanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 118006058HCID 118006058, compound2×

Product 1

HCID 178437401HCID 178437401, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
220 °C

Procedure

A mixture containing methyl 2-(4-(1H-pyrazol-1-yl)benzyl)-3-oxopentanoate (2.7 g, 9.4 mmol, Intermediate 32: step b), 4-bromoaniline (1.6 g, 9.4 mmol), and para-toluenesulfonic acid monohydrate (162 mg, 0.943 mmol) in diphenyl ether (31 mL) was heated to 220° C. After 2 hours, the flask was cooled to 23° C. Diethyl ether (50 mL) was added resulting in the formation of a solid. The heterogeneous mixture was stirred at 23° C. After 30 minutes, the mixture was filtered through filter paper and the filter cake was rinsed with diethyl ether. The solids were collected and dried to afford the title compound which was taken onto the next step without further purification.

Workup

  1. temperaturethe flask was cooled to 23° C
  2. customresulting in the formation of a solid
  3. waitAfter 30 minutes
  4. filtrationthe mixture was filtered
  5. filtrationthrough filter paper
  6. washthe filter cake was rinsed with diethyl ether
  7. customThe solids were collected
  8. customdried

Sources & evidence

ORD record
ord-abda46d48f8e4ea5af06827114e5aeb4
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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