Tetrahydro-4H-pyran-4-one → 4-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-YL)tetrahydro-2H-pyran-4-OL

HRID 473646Notes

Reaction equation

HRID 473646 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.[O:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1>C1COCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]([C:30]3([OH:33])[CH2:31][CH2:32][O:27][CH2:28][CH2:29]3)=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 59373954N-(4-(3-bromopyridin-2-yloxy)phenyl)pyridin-2-amineHCID 178418918HCID 178418918, compound2×

Product 1

HCID 593741514-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-YL)tetrahydro-2H-pyran-4-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(4-(3-bromopyridin-2-yloxy)phenyl)pyridin-2-amine (1 g, 2.92 mmol) in THF (10 mL) at room temperature was added isopropylmagnesium chloride (5.11 mL, 10.23 mmol). After 1 h stirring at room temperature, another equal amount of isopropylmagnesium chloride was added and the resulting mixture was stirred at room temperature overnight. To the solution was added dropwise dihydro-2H-pyran-4(3H)-one (0.540 mL, 5.84 mmol) and stirring was continued for 1 h. Reaction was quenched with saturated NH4Cl and extracted with DCM. Purification by Biotage produced the product. MS (ESI, pos. ion) m/z: 364.0. IC50 (uM) 0.04172.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. stirringstirring
  3. waitwas continued for 1 h
  4. customReaction
  5. customwas quenched with saturated NH4Cl
  6. extractionextracted with DCM
  7. customPurification by Biotage
  8. customproduced the product

Sources & evidence

ORD record
ord-0de224f8a61f41c0a325f9ff50552071
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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