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N-(3-Bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide → N-(3-cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide

HRID 556312
Notes
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Reaction equation

HRID 556312 reaction equation
[Br-].[CH:2]1([Zn+])[CH2:4][CH2:3]1.Br[C:7]1[N:11]2[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:2]1([C:7]2[N:11]3[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 57607463N-(3-Bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide2×HCID 178419765HCID 178419765, compound2×

Product 1

HCID 57607458N-(3-cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×
HCID 8028
Tetrahydrofuran
Solvent
3×

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.0797 g, 0.000069 mol) was added to a solution of 0.50 M of cyclopropylzinc bromide in tetrahydrofuran (4.1 mL) and N-(3-bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide (compound d, 0.225 g, 0.000690 mol) in tetrahydrofuran (20.0 mL) and the reaction was heated to reflux for 3 hours. An additional 0.50 M of cyclopropylzinc bromide (4.1 mL) in tetrahydrofuran and tetrakis(triphenylphosphine)palladium(0)(0.080 g) was added and the mixture was heated to reflux overnight. The reaction was concentrated in vacuo and crude product purified by column chromatography (50% ethyl acetate/hexanes) to give N-(3-cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide as a yellow solid. Rf 0.46, 50% ethyl acetate/hexanes; MS m/z 287 (M+H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureto reflux overnight
  5. concentrationThe reaction was concentrated in vacuo and crude product
  6. custompurified by column chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d38e5188f66d48a4b238dde5d3f52ecf
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08058274B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes