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

HRID 527994
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인쇄 미리보기

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HRID 527994 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15](I)[N:14]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH:38]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:37]4[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH:38]=4)[N:14]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 90417868HCID 90417868, 화합물

생성물 1

HCID 90418550tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

시약·촉매·용매 3

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 20074477Dimethoxyethane ethanol용매

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온도
100 °C

실험 절차

To a solution of Example 3C (3.07 g, 6.03 mmol) in 70 mL 1,2-dimethyoxyethane/ethanol (50:20) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.80 g, 9.04 mmol), 2M sodium carbonate (12.06 mL, 24.11 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.423 g, 0.603 mmol). The mixture was stirred at 100° C. for 3 hours, cooled and diluted with 50 mL ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica (Analogix 280) eluting with a gradient of 20% to 80% ethyl acetate/hexane gave the title compound. MS (ESI+) m/z 565.43 (M+H)+.

후처리

  1. temperaturecooled
  2. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica (Analogix 280)
  7. washeluting with a gradient of 20% to 80% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-c6ab07f1b19a415ebf783a58404fbeb8
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346813B2

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