3,4-dihydro-2H-pyran → N-(4-(3-(3,4-dihydro-2H-pyran-2-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

HRID 410232Notes

Reaction equation

HRID 410232 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(N(C)C2CCCCC2)CCCCC1.[O:39]1[CH:44]=[CH:43][CH2:42][CH2:41][CH2:40]1>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCOCC1>[O:39]1[CH:40]=[CH:41][CH2:42][CH2:43][CH:44]1[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 24210N-Methyl dicyclohexylamineHCID 59326883N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Product 1

HCID 59326996N-(4-(3-(3,4-dihydro-2H-pyran-2-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A 25 mL reseable vial was charged with bis(tri-tert-butylphosphine) palladium (0) (83 mg, 0.163 mmol) and N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (650 mg, 1.632 mmol). The vial was sealed and placed under an atmosphere of nitrogen. After addition of dioxane (5.38 ml), N-cyclohexyl-N-methylcyclohexanamine (1.072 ml, 4.90 mmol) and 3,4-dihydro-2H-pyran (549 mg, 6.53 mmol) were added and the mixture was heated to 105° C. Following complete consumption of the starting material, the reaction mixture was cooled to room temperature and transferred to a 100 mL round bottom flask, and the solvent was removed under reduced pressure. Following purification by silica gel chromatography the desired product was obtained as a racemic mixture. MS (ESI, pos. ion) m/z: 402.0 (M+1).

Workup

  1. customThe vial was sealed
  2. additionwere added
  3. customconsumption of the starting material
  4. temperaturethe reaction mixture was cooled to room temperature
  5. customtransferred to a 100 mL round bottom flask
  6. customthe solvent was removed under reduced pressure
  7. custompurification by silica gel chromatography the desired product
  8. customwas obtained as a racemic mixture

Sources & evidence

ORD record
ord-39399b281bf14feda5aedbb6c58f188d
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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