Cesium carbonate → HCID 86684149, 화합물

HRID 1024082노트

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HRID 1024082 반응식
Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=[C:4]([Cl:19])[CH:3]=1.[O:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=3)[CH2:26][CH2:25]2)[CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>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].O1CCOCC1>[Cl:19][C:4]1[CH:3]=[C:2]([NH:36][C:33]2[CH:32]=[CH:31][C:30]([N:27]3[CH2:28][CH2:29][N:24]([CH:22]4[CH2:21][O:20][CH2:23]4)[CH2:25][CH2:26]3)=[CH:35][N:34]=2)[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866841255-(4-(Oxetan-3-yl)piperazin-1-yl)pyridin-2-amineHCID 866841484-Bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole

생성물 1

HCID 86684149HCID 86684149, 화합물수율 85%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A microwave vial equipped with a magnetic stirrer was charged with 4-bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole 116a (600 mg, 1.65 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (390 mg 1.67 mmol), cesium carbonate (1.09 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium(0) (152 mg, 0.167 mmol), Xantphos (193 mg, 0.334 mmol), and dioxane (10 mL). After bubbling nitrogen through the suspension for 10 minutes, the reaction was heated at 120° C. overnight. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was washed with a mixed solvent of petroleum ether and ethyl acetate (15 mL, 2:1) to afford 118a as a yellow solid (720 mg, 85%). MS-ESI: [M+H]+ 515.2

후처리

  1. customA microwave vial equipped with a magnetic stirrer
  2. customAfter bubbling nitrogen through the suspension for 10 minutes
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was washed with a mixed solvent of petroleum ether and ethyl acetate (15 mL, 2:1)

출처 및 근거

ORD 기록
ord-d31926d161154cc8afc4dbf8a99f6b16
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722676B2

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