Toluene → N-(3-Fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamide

HRID 84384Notes

Reaction equation

HRID 84384 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:29]([C:31]4([C:34]([NH2:36])=[O:35])[CH2:33][CH2:32]4)=[O:30])=[CH:24][C:23]=3[F:43])[CH:13]=2)=[N:10][CH:11]=1.C1(C)C=CC=CC=1>CC(C)=O.O.C(O)(C(F)(F)F)=O>[F:43][C:23]1[CH:24]=[C:25]([N:28]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:29]([C:31]2([C:34]([NH2:36])=[O:35])[CH2:33][CH2:32]2)=[O:30])[CH:26]=[CH:27][C:22]=1[O:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][N:10]=3)[S:20][C:19]=12

Participants

6

Reactant 2

HCID 1140TolueneHCID 66599014N-(4-(2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Product 1

HCID 86635186N-(3-Fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamideYield 103%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 140 (0.22 g, 0.37 mmol) was dissolved in acetone (50 mL) to give a colorless solution. The reaction mixture was diluted with water (20 mL) and TFA (2 mL), and heated to reflux for 2 h. It was then cooled and concentrated. The precipitated product was isolated by suction filtration. A small amount of toluene (5 mL) was added to the wet solid, and the mixture was concentrated to remove water azeotropically. The residue was dried in vacuum to provide aldehyde 141 (0.21 g, 103% yield). MS (m/z): 553.2 (M+H).

Workup

  1. customto give a colorless solution
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. temperatureIt was then cooled
  5. concentrationconcentrated
  6. customThe precipitated product was isolated by suction filtration
  7. concentrationthe mixture was concentrated
  8. customto remove water azeotropically
  9. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-6118a793550e4fb9a680e950db99274d
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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