Potassium Carbonate → 3-Methoxy-5-(2-phenyl-4-(pyridin-4-yl)thiazol-5-yl)pyridin-2-amine

HRID 538425

반응식

HRID 538425 반응식
Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[CH3:19][O:20][C:21]1[C:22]([NH2:36])=[N:23][CH:24]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:26]=1.C([O-])([O-])=O.[K+].[K+]>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>[CH3:19][O:20][C:21]1[C:22]([NH2:36])=[N:23][CH:24]=[C:25]([C:2]2[S:6][C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:4][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:26]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 533980593-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 665905405-Bromo-2-phenyl-4-(pyridin-4-yl)thiazole

생성물 1

HCID 591376043-Methoxy-5-(2-phenyl-4-(pyridin-4-yl)thiazol-5-yl)pyridin-2-amine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-bromo-2-phenyl-4-(pyridin-4-yl)thiazole (20 mg, 0.062 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (39 mg, 0.157 mmol), and aqueous 2.0 M K2CO3 solution (0.5 ml, 1 mmol) in dioxane (0.5 mL) was sparged with Ar. Pd(PPh3)4 (181 mg, 0.157 mmol) was added, the reaction was sealed and irradiated at 120° C. for 15 min. While allowing to cool to rt, the reaction partitioned and the resulting layers were separated. The aqueous phase was extracted with EtOAc (3×) and the combined organic phases were washed with brine, dried (Na2SO4), and concentrated. The resulting residue was purified by reverse phase HPLC to give, after freeze drying, 3-methoxy-5-(2-phenyl-4-(pyridin-4-yl)thiazol-5-yl)pyridin-2-amine as the TFA salt: LCMS (m/z): 361.0 (MH+), tR=0.58 min.

후처리

  1. customwas sparged with Ar
  2. customthe reaction was sealed
  3. customirradiated at 120° C. for 15 min
  4. customthe reaction partitioned
  5. customthe resulting layers were separated
  6. extractionThe aqueous phase was extracted with EtOAc (3×)
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe resulting residue was purified by reverse phase HPLC
  11. customto give
  12. customafter freeze drying

출처 및 근거

ORD 기록
ord-b1ec43678c014042ad82e9af5f9403ca
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865732B2

연결된 노트

불러오는 중…