Dimethylformamide → HCID 68764339, 화합물

HRID 387541

반응식

HRID 387541 반응식
[CH:1]1([C:4]2[C:5]([N:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[C:6]3[C:12](I)=[N:11][N:10]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C=O)C.[CH:48]([C:50]1[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=1)=[CH2:49]>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:1]1([C:4]2[C:5]([N:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[C:6]3[C:12](/[CH:49]=[CH:48]/[C:50]4[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=4)=[N:11][N:10]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 142723-VinylpyridineHCID 68761344tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

생성물 1

HCID 68764339HCID 68764339, 화합물수율 81%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A 50 mL round bottom flask charged with tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (500 mg, 0.85 mmol), triethylamine (355 μL, 2.54 mmol), Pd2dba3 (19.4 mg, 0.021 mmol), tri-o-tolylphosphine (19.4 mg, 0.064 mmol), and DMF (7 mL) was purged under N2 (3 cycles). 3-vinylpyridine (270.24 mg, 1.7 mmol) was added, and the mixture was stirred at 100° C. under a N2 atmosphere for 6 hours. The reaction mixture was cooled to room temperature, diluted with warm EtOAc (100 mL) and washed with water (2×30 mL). The phases were separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (Biotage Flash 40S+) eluting with 25% EtOAc/hexane followed by 50% EtOAc/hexane to provide (E)-tert-butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-(2-(pyridin-3-yl)vinyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (390 mg, 81% yield) as a solid. LCMS (APCI+) m/z 567.3 (M+H)+.

후처리

  1. customwas purged under N2 (3 cycles)
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with water (2×30 mL)
  4. customThe phases were separated
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (Biotage Flash 40S+)
  9. washeluting with 25% EtOAc/hexane

출처 및 근거

ORD 기록
ord-7e5cc159f70246e486a35fe9f728e2e4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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