Water → (4-Methoxy-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

HRID 1713651Notes

Reaction equation

HRID 1713651 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[N:4][CH:3]=1.[S:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.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>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5]2[S:6][C:2]([C:18]3[CH:19]=[CH:20][S:16][CH:17]=3)=[CH:3][N:4]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 12348632(5-Bromo-thiazol-2-yl)-(4-methoxy-phenyl)-amine

Product 1

HCID 11162034(4-Methoxy-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (5-bromo-thiazol-2-yl)-(4-methoxy-phenyl)-amine (203 mg, 0.710 mmol), 3-thiophene-boronic acid (268 mg, 2.10 mmol, 6.0 equiv), Pd(PPh3)4 (12 mg, 0.0105 mmol, 0.03 equiv), Na2CO3 (326 mg, 3.08 mmol, 8.8 equiv), and water (305 μL, 16.7 mmol, 24 equiv) in toluene (10 mL) is heated in a sealed tube to 120° C. for 1 h, under an argon atmosphere. The resulting suspension is allowed to cool to RT and filtered through a pad of celite, washing the filter cake with CH2Cl2 and water. The layers are separated. The organic phase is dried (Na2SO4), filtered and concentrated. Purification by MPLC (CH3CN/H2O/TFA) affords the title compound as a light beige solid: ES-MS: 289.0 [M+H]+; single peak at tR=7.43 min (System 1); Rf=0.56 (CH2Cl2/MeOH, 80/20).

Workup

  1. temperatureto cool to RT
  2. filtrationfiltered through a pad of celite
  3. washwashing the filter cake with CH2Cl2 and water
  4. customThe layers are separated
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by MPLC (CH3CN/H2O/TFA)

Sources & evidence

ORD record
ord-d00c10974cef49dab8c50a9f904e1b97
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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