4-Bromoaniline → HCID 67486134, compound

HRID 2371295Notes

Reaction equation

HRID 2371295 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2([CH:21]3[CH2:26][CH2:25][CH:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22]3)C(=O)OC(C)(C)O[C:12]2=[O:20])=[CH:6][CH:5]=1.[Br:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1.C(OCC)(=O)C.CCCCCC>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:12](=[O:20])[NH:37][C:36]2[CH:38]=[CH:39][C:33]([Br:32])=[CH:34][CH:35]=2)[CH:21]2[CH2:22][CH2:23][CH:24]([C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:25][CH2:26]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 21226206Ethyl acetate hexane2×HCID 67486780HCID 67486780, compound

Product 1

HCID 67486134HCID 67486134, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 1 eq (2.32 mmol) of 4-[5-(4-tert-Butyl-cyclohexyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl]-benzoic acid methyl ester was added 1.5 eq (3.5 mmol) of 4-bromoaniline in 2 mL of n-methyl-pyrrolidinone in a microwave vial. The reaction was run for eight minutes at 220 degrees C. The reaction mixture was worked up by partitioning with ethyl acetate/diethyl ether (1:1)/1 N HCl. Product was isolated by chromatography gradient: 10% ethyl acetate/hexane to 40% ethyl acetate hexane.

Workup

  1. customby partitioning with ethyl acetate/diethyl ether (1:1)/1 N HCl
  2. customProduct was isolated by chromatography gradient

Sources & evidence

ORD record
ord-285a2236df7640f0a190ddd93091ddb1
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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