Diisopropylethylamine → N-(4-bromo-3-nitrophenyl)-3-(2-cyanopropan-2-yl)benzamide

HRID 1184871Notes

Reaction equation

HRID 1184871 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)([CH3:5])[CH3:4])#[N:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Br:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][C:50]=1[N+:56]([O-:58])=[O:57]>CN(C=O)C>[Br:48][C:49]1[CH:55]=[CH:54][C:52]([NH:53][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][CH:14]=[C:6]([C:3]([C:1]#[N:2])([CH3:4])[CH3:5])[CH:7]=2)=[CH:51][C:50]=1[N+:56]([O-:58])=[O:57]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6122994-Bromo-3-nitroanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 571495383-(2-Cyanopropan-2-yl)benzoic acid

Product 1

HCID 67125575N-(4-bromo-3-nitrophenyl)-3-(2-cyanopropan-2-yl)benzamideYield 249.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(2-cyanopropan-2-yl)benzoic acid 3 (436 mg, 2.304 mmol), HATU (1.051 g, 2.76 mmol) and DIPEA (0.762 mL, 4.61 mmol) in DMF (9 mL) was stirred 15 min at rt. 4-bromo-3-nitroaniline (200 mg, 0.922 mmol) was added and stirred overnight at 60° C. The reaction mixture was cooled to rt and extracted with CH2Cl2. Organic layer was washed (3×) with water, dried and evaporated. Purification by chromatography heptane:EtOAc (1:1) gave N-(4-bromo-3-nitrophenyl)-3-(2-cyanopropan-2-yl)benzamide 61 (894 mg, 89%). (m/z)=388 and 390 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with CH2Cl2
  3. washOrganic layer was washed (3×) with water
  4. customdried
  5. customevaporated
  6. customPurification by chromatography heptane:EtOAc (1:1)

Sources & evidence

ORD record
ord-7e302f0d58dd47a98260c33f41f27f87
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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