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Cesium carbonate → 3-Fluoro-5-(1,3-thiazol-5-yl)aniline

HRID 410568
Notes
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Reaction equation

HRID 410568 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:8]=1)[NH2:5].Br[C:19]1[S:20][CH:21]=[N:22][CH:23]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:19]2[S:20][CH:21]=[N:22][CH:23]=2)[CH:8]=1)[NH2:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 5460595-BromothiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 597700393-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 672565063-Fluoro-5-(1,3-thiazol-5-yl)anilineYield 85%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
95 °C

Procedure

The product of Step 1 (2.66 g, 11.22 mmol), 2-bromo-1,4-thiazole (1.003 mL, 11.22 mmol), Pd2(dba)3 (0.514 g, 0.561 mmol), X-phos (0.535 g, 1.122 mmol), and cesium carbonate (7.31 g, 22.44 mmol) were added to a dry flask. Degassed with argon, then added dioxane (25 mL) and water (2.5 mL). The reaction mixture was degassed with argon for five minutes, and then heated to 95° C. After 16 hours, the reaction mixture was cooled, diluted with ethyl acetate, filtered through celite, and concentrated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate and hexanes to afford 3-fluoro-5-(1,3-thiazol-5-yl)aniline (2.27 g, 9.49 mmol, 85%). MS ESI: [M+H]+ m/z 195.1.

Workup

  1. customDegassed with argon
  2. customThe reaction mixture was degassed with argon for five minutes
  3. temperaturethe reaction mixture was cooled
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-5c2a627510b042b8b8af3848db8c87ad
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759366B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes