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1,4-Dioxane → 7-Chloro-3-(2,4-difluorophenyl)thieno[3,2-b]pyridine

HRID 871173
Notes
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Reaction equation

HRID 871173 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([Cl:11])=[C:5]2[S:4][CH:3]=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1B(O)O.O1CCOCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:11][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[C:2]([C:16]3[CH:15]=[CH:14][C:13]([F:12])=[CH:18][C:17]=3[F:19])=[CH:3][S:4][C:5]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27343342,4-Difluorophenylboronic acidHCID 867304243-Bromo-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 867304267-Chloro-3-(2,4-difluorophenyl)thieno[3,2-b]pyridineYield 360.6%

Reagents, catalysts & solvents 2

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A vessel capable of sealing was charged with a mixture of 3-bromo-7-chlorothieno[3,2-b]pyridine (110 mg, 0.443 mmol), 2,4-difluorophenylboronic acid (84 mg, 0.531 mmol), PdCl2(dppf)-CH2Cl2 adduct (18.1 mg, 0.022 mmol), dioxane (3 mL), and a 2.0 M aqueous solution of K3PO4 (0.66 mL, 1.328 mmol) and was purged with nitrogen for 10 min. The vessel was sealed and heated at 90° C. for 3 hours. Upon cooling, the reaction mixture was diluted with water and extracted with CH2Cl2. The combined organics were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by BIOTAGE® eluting with 30%-60% CH2Cl2/hexanes at 30 mL/min. Concentration of appropriate fractions provided the title compound (450 mg, 49% yield) as a white powder. LC/MS: Example 102A @ 3.60 min (RT) (Condition G). MS (ES): m/z=282.02/284.02, [M+H]+.

Workup

  1. customThe vessel was sealed
  2. temperatureUpon cooling
  3. extractionextracted with CH2Cl2
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by BIOTAGE®
  8. washeluting with 30%-60% CH2Cl2/hexanes at 30 mL/min

Sources & evidence

ORD record
ord-5459e006487a4f3bb4269a29fac2c772
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969586B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes