Water → P-Anisidine

HRID 1043666Notes

Reaction equation

HRID 1043666 reaction equation
IC1N2C(SC([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=N2)=NC=1.CN(C1C=C(B(O)O)C=CC=1)C.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.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>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([NH2:10])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27625273-(Dimethylamino)benzeneboronic acidHCID 67333843(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine

Product 1

HCID 7732P-AnisidineYield 32.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine (55 mg, 0.10 mmol) was suspended in 1,4-dioxane (1 mL) at room temperature and argon was bubbled into the mixture while tetrakis(triphenylphosphine)palladium(0) (0.011 mmol, 12 mg), 3-(N,N-dimethylamino)phenylboronic acid (0.202 mmol, 33 mg), cesium carbonate (0.268 mmol, 88 mg) and water (1 mL) were added. The mixture was deoxygenated for 10 minutes and heated under microwave irradiation at 140° C. for 1 hour. On cooling, the mixture was diluted with dichloromethane, adsorbed in silica and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8). The obtained residue was further purified by preparative HPLC to give {5-[3-dimethylaminophenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]}-(4-methoxyphenyl)-amine as a white solid (4 mg, 7% yield).

Workup

  1. additionwere added
  2. customThe mixture was deoxygenated for 10 minutes
  3. temperatureOn cooling
  4. additionthe mixture was diluted with dichloromethane
  5. custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8)
  6. customThe obtained residue was further purified by preparative HPLC

Sources & evidence

ORD record
ord-24e5547bd4a74042876c3380997a7ef5
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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