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

HRID 1039914
Notes
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Reaction equation

HRID 1039914 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, 11.2 mmol), 2-bromo-1,4-thiazole (1.00 ml, 11.2 mmol), Pd2(dba)3 (0.514 g, 0.561 mmol), X-phos (0.535 g, 1.122 mmol), and cesium carbonate (7.31 g, 22.4 mmol) were added to a dry flask. The flask was degassed with argon, then dioxane (25 ml) and water (2.5 ml) were added. 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 flash chromatography (EtOAc/hexane gradient) to afford 3-fluoro-5-(1,3-thiazol-5-yl)aniline (2.27 g, 9.49 mmol, 85% yield). MS APCI: [M+H]+ m/z 195.1. 1H NMR (500 MHz, DMSO-d6) δ 9.02 (s, 1H); 8.18 (s, 1H); 6.66-6.62 (m, 1H); 6.61-6.59 (m, 1H); 6.29-6.26 (m, 1H); 5.58 (s, 2H).

Workup

  1. customThe flask was degassed with argon
  2. additiondioxane (25 ml) and water (2.5 ml) were added
  3. customThe reaction mixture was degassed with argon for five minutes
  4. temperaturethe reaction mixture was cooled
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered through celite
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-597bffccfc6349d5aae97d605229cd6f
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551984B2

Reaction notes

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