Sodium Bicarbonate → tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

HRID 527989

반응식

HRID 527989 반응식
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)(O)[O-].[Na+].[F:29][C:30]1[CH:31]=[CH:32][C:33]([O:39][CH3:40])=[C:34](B(O)O)[CH:35]=1>CN(C)C=O.O.C(OCC)(=O)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:39][CH3:40])=[C:32]([C:2]2[C:3]3[CH:10]=[C:9]([CH:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:31]=1

참가 물질

8

반응물 3

HCID 516892Sodium BicarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 90418107tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

생성물 1

HCID 90418838tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

시약·촉매·용매 4

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a solution of Example 1C (200 mg, 0.6 mmol) in N,N-dimethylformamide (8 mL), was added a solution of sodium bicarbonate (0.118 g, 1.404 mmol) in 0.5 mL water followed by 5-fluoro-2-methoxyphenylboronic acid (204 mg, 1.2 mmol). The mixture was degassed with nitrogen and [1,1′-bis(di tert butyl phosphino)ferrocene]palladium(II) dichloride (21 mg, 0.033 mmol) was added. The mixture was heated under microwave conditions (Biotage Initiator) at 100° C. for 1 hour. The mixture was diluted with ethyl acetate and filtered through diatomaceous earth. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (silica gel, 40% ethyl acetate-hexane) to afford the title compound. LCMS: 427.21 (M+1)+.

후처리

  1. additionwas added
  2. filtrationfiltered through diatomaceous earth
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography (silica gel, 40% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-8b01117117ae4def8e3a9bfba393835a
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346813B2

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