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Dimethylformamide → 2,2,2-trifluoro-N-(6-formylimidazo[1,2-a]pyridin-2-yl)acetamide

HRID 69195
Notes
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Reaction equation

HRID 69195 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][N:9]2[CH:15]=1)=[O:4].C([Mg]Cl)(C)C.CN([CH:26]=[O:27])C.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([CH:26]=[O:27])=[CH:10][N:9]2[CH:15]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 110136782,2,2-trifluoro-N-(6-iodoimidazo[1,2-a]pyridin-2-yl)acetamideHCID 178418918HCID 178418918, compound

Product 1

HCID 120659512,2,2-trifluoro-N-(6-formylimidazo[1,2-a]pyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Conditions

Temperature
-40 °C

Procedure

2,2,2-Trifluoro-N-(6-iodo-imidazo[1,2-a]pyridin-2-yl)-acetamide (Stage 153.2, 1 g, 2.82 mmol) was dissolved in THF (15 mL) and cooled down to −40° C. under nitrogen atm. iPrMgCl in THF (2 M, 2.8 mL) was added dropwise. After 1 h stirring, cold DMF (0.65 mL, 8.46 mmol) in THF (1 mL) was added and the RM warmed up to −10° C. in 4 h. NH4Cl solution was added and the mixture was extracted 3 times with EtOAc. Combined organic layers were washed with brine and dried on Na2SO4. After evaporation of the solvent the crude was purified by preparative HPLC with acetonitrile/water (with 0.1% TFA) to afford the title compound (tR 0.88 min (conditions 2), (MH+=258).

Workup

  1. temperaturethe RM warmed up to −10° C. in 4 h
  2. extractionthe mixture was extracted 3 times with EtOAc
  3. washCombined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customAfter evaporation of the solvent the crude
  6. customwas purified by preparative HPLC with acetonitrile/water (with 0.1% TFA)

Sources & evidence

ORD record
ord-e232d6d6e2ea446ba1e20fb207ed419d
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822468B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes