Cesium carbonate → N-(4-(3-Iodopyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 410307Notes

Reaction equation

HRID 410307 reaction equation
F[C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[I:8][C:7]1[C:2]([O:25][C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:10]3[S:9][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[N:11]=3)=[CH:24][CH:23]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 70095012-Fluoro-3-iodopyridineHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenol

Product 1

HCID 59327141N-(4-(3-Iodopyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 2-fluoro-3-iodopyridine (1.674 g, 7.51 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (2.73 g, 11.26 mmol) and cesium carbonate (4.16 g, 12.76 mmol) in N-methyl-2-pyrrolidinone (10 mL) was degassed and heated to 120° C. After 3 h 30 min, the reaction was cooled to 23° C., diluted with EtOAc (200 mL) and washed with water (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 0-1% methanol/dichloromethane), affording the product as an off-white solid. MS (ESI, pos. ion) m/z: 445.9 (M+1).

Workup

  1. customwas degassed
  2. temperaturethe reaction was cooled to 23° C.
  3. additiondiluted with EtOAc (200 mL)
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (eluant: 0-1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-130ac43078d644b685c71e3c99d7811b
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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