Cesium carbonate → 7-(2-fluoro-4-nitrophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine

HRID 418734Notes

Reaction equation

HRID 418734 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12](I)[S:13][C:6]=12.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([NH:33][C:32]3[CH:34]=[CH:35][CH:36]=[C:30]([O:29][CH3:28])[CH:31]=3)[S:13][C:6]=12

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 108243-MethoxyanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 594576617-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine

Product 1

HCID 594576847-(2-fluoro-4-nitrophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amineYield 59%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 399 (scheme 87) (700 mg, 1.68 mmol), Cs2CO3 (1.12 g, 3.43 mmol), 3-methoxyaniline (190 μL, 206 mg, 1.68 mmol), Pd(OAc)2 (70 mg, 0.17 mmol) and Xantphos (1.43 g, 2.52 mmol) (J. Org. Chem., 1999, 64, 6019-6022) in dioxane (15 mL) was heated to reflux for 5 hrs. The reaction mixture was cooled, concentrated and the residue was purified by flash chromatography using 80% EtOAc in hexanes as the eluent, to afford 403 (408 mg, 59% yield). MS (m/z): (M+1) 412.0 (100%).

Workup

  1. temperatureto reflux for 5 hrs
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fa750a219dd04d45ae39e8d44f6f5fd6
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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