2,6-Diethyl-3-nitroaniline → HCID 59800734, compound

HRID 656713Notes

Reaction equation

HRID 656713 reaction equation
ClC1C=CC([C@@H:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14](OC)=[CH:13][C:12]=2F)C)=CC=1.C([C:22]1[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[C:24]([CH2:31][CH3:32])[C:23]=1N)C>>[CH2:31]([C:24]1[CH:23]=[CH:22][C:27]([NH:28][CH2:13][C:14]2[CH:8]=[N:10][C:11]([CH3:12])=[CH:16][CH:15]=2)=[CH:26][CH:25]=1)[CH3:32]

Participants

3

Reactant 2

HCID 141461072,6-Diethyl-3-nitroanilineHCID 59800732HCID 59800732, compound

Product 1

HCID 59800734HCID 59800734, compoundYield 48%

Procedure

292 μl (2.085 mmol; 5 eq.) of (S)-4-chlora-alpha-methylbenzylamine (3) react according to GP-1B with 76 mg (0.417 mmol; 1.0 eq.) of 2-hydroxymethyl-4-methoxybenzyl-boronic acid (2). Flash chromatographical purification (hexane/ethylacetate 10:1) yields 58.6 mg (0.2 mmol; 48%) of the desired amine 4.

Workup

  1. customFlash chromatographical purification (hexane/ethylacetate 10:1)

Sources & evidence

ORD record
ord-43895db5158c406585e0e14c54c90937
Source dataset
uspto-grants-2011_12
Patent number
US08071810B2

Reaction notes

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