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Cesium fluoride → 3-(5-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-2-yloxy)-N,N-dimethylpropan-1-amine

HRID 418728
Notes
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Reaction equation

HRID 418728 reaction equation
Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[CH:3]=1.[CH3:22][N:23]([CH3:43])[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.[F-].[Cs+].C(=O)(O)[O-].[Na+]>COCCOC.O.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>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[C:2]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:23]([CH3:22])[CH3:43])=[N:29][CH:30]=3)[S:10][C:9]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 17998906N,N-Dimethyl-3-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxy)propan-1-amineHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 587903463-(5-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-2-yloxy)-N,N-dimethylpropan-1-amine
Yield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Bromothienopyridine 50 (1.22 g, 3.30 mmol), N,N-dimethyl-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)propan-1-amine (1.15 g, 3.76 mmol), and tetrakis(triphenylphosphine)palladium (0.14 g, 0.12 mmol) were dissolved in dry DME (100 mL). Cesium fluoride (1.51 g, 10.0 mmol) and sodium bicarbonate (0.81 g, 9.6 mmol) were dissolved in water (5 ml each) and added to the reaction mixture, which was degassed with a stream of N2, then heated to reflux for 4 h, cooled, and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was collected, washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. The resulting orange solid was triturated with ether to provide 379 (1.12 g, 75% yield). LRMS (M+H): 469.2.

Workup

  1. additionadded to the reaction mixture, which
  2. customwas degassed with a stream of N2
  3. temperatureheated
  4. temperatureto reflux for 4 h
  5. temperaturecooled
  6. concentrationconcentrated
  7. customThe residue was partitioned between ethyl acetate and water
  8. customThe organic phase was collected
  9. washwashed with brine
  10. dry with materialdried (anhydrous MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe resulting orange solid was triturated with ether

Sources & evidence

ORD record
ord-df937bfb38384629b1fa9fdfccbde3e6
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093264B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes