Ammonium formate → 5-Ethyl-2-[2-fluoro-4-(3-hydroxy-propylamino)-phenoxy]-phenol

HRID 1023947노트

반응식

HRID 1023947 반응식
C([O:8][C:9]1[CH:27]=[C:26]([CH2:28][CH3:29])[CH:25]=[CH:24][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:14][C:13]=1[F:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:28]([C:26]1[CH:25]=[CH:24][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:14][C:13]=2[F:23])=[C:9]([OH:8])[CH:27]=1)[CH3:29]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 591912673-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenylamino]-propan-1-ol

생성물 1

HCID 591913445-Ethyl-2-[2-fluoro-4-(3-hydroxy-propylamino)-phenoxy]-phenol수율 45.4%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

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온도
65 °C

실험 절차

3-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenylamino]-propan-1-ol (400 mg, 1.01 mmol) was taken in 15 ml of absolute ethanol, under nitrogen. To this was added Pd(OH)2, (20%, 50 mg) followed by ammonium formate (200 mg, 3.1 mmol). The reaction mixture was heated at 65° C. and monitored by TLC. After complete consumption of starting material (20 minutes), the heating was stopped and mixture cooled to rt. The reaction mixture was filtered through celite and the residue was washed with methanol. The combined filtrate was concentrated to obtain 300 mg of crude compound showing 70% by HPLC. The crude was purified by preparative HPLC (Column: C18 Symmetry (300×19 mm), 7μ, Mobile phase A: 20 mM ammonium acetate, Mobile phase B: Acetonitrile) to get 140 mg (45.3%) of title compound.

후처리

  1. customAfter complete consumption of starting material (20 minutes)
  2. temperaturemixture cooled to rt
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe residue was washed with methanol
  5. concentrationThe combined filtrate was concentrated
  6. customto obtain 300 mg of crude compound
  7. customThe crude was purified by preparative HPLC (Column: C18 Symmetry (300×19 mm), 7μ, Mobile phase A: 20 mM ammonium acetate, Mobile phase B: Acetonitrile)

출처 및 근거

ORD 기록
ord-d7cc3cf57c8a49cab9f49add60016609
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722746B2

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