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Diisopropylethylamine → HCID 86723801, compound

HRID 577575
Notes
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Reaction equation

HRID 577575 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH2:19][NH:20][CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([N:20]([CH2:21][CH2:22][OH:23])[CH2:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:25][CH:24]=1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1044692-[(4-Methoxybenzyl)amino]ethanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 847957933-Bromo-6-fluoro-2-methylbenzoic acid

Product 1

HCID 86723801HCID 86723801, compoundYield 420.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-6-fluoro-2-methylbenzoic acid (Cpd QQ, 4.8 g, 2.4 mmol), 2-[(4-methoxybenzyl)amino]ethanol (130a, 5.5 g, 23 mmol) and DIPEA (8 g, 62 mmol) in dry DMF (80 mL) was added HATU (12 g, 31 mmol). The mixture was stirred at room temperature for 14 hours. To the reaction mixture was added EtOAc (130 mL). The solution was washed with brine (4×60 mL), dried over Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 2/1) to give 3-bromo-6-fluoro-N-(2-hydroxyethyl)-N-(4-methoxybenzyl)-2-methylbenzamide (130b, 4 g, 48.8%) as a colorless oil.

Workup

  1. washThe solution was washed with brine (4×60 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography (petroleum ether/EtOAc, 2/1)

Sources & evidence

ORD record
ord-35b2e077392f4fbfa5d2b1364b8a5bfe
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040515B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes