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Acetonitrile → N-[5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539760
Notes
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Reaction equation

HRID 539760 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[C:15]([CH:17]=3)[NH2:16])[N:10]=2)[CH:7]=1.C(#N)C.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[C:15]([NH:16][C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[CH:17]=3)[N:10]=2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 575162715-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)aniline

Product 1

HCID 67985680N-[5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamideYield 37%

Reagents, catalysts & solvents 1

HCID 1049Pyridine
Solvent

Conditions

Temperature
80 °C

Procedure

A 20 mL vial is charged with 5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)aniline (0.463 g, 0.0013 mol), acetonitrile (7 mL) and pyridine (0.210 mL). The mixture is added trimethylacetyl chloride (0.320 mL, 2.6 mmol) and stirred for 20 min at 80° C. The solution is concentrated, taken into EtOAc (10 mL) and washed once with HCl (10 mL, 1M) and NaOH (10 mL, 1M). Organics are dried, concentrated, and purified on silica (0-100% EtOAc in Hexanes) to give the title compound (212 mg, 37% yield). LCMS m/z=440.4 [M+H]+, tR=2.67 min.

Workup

  1. concentrationThe solution is concentrated
  2. washwashed once with HCl (10 mL, 1M) and NaOH (10 mL, 1M)
  3. customOrganics are dried
  4. concentrationconcentrated
  5. custompurified on silica (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-6c2c5c1bbace4578b7f7f4572bcc334c
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871767B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes