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Potassium Carbonate → HCID 178432608, 화합물

HRID 1530605
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HRID 1530605 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:20])[C:6]=1[CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1.[CH3:21][C:22]1[N:26]=[C:25]([C:27]2[N:28]=[C:29]3[N:39]([CH:40]=2)[CH2:38][CH2:37][O:36][C:35]2[C:30]3=[CH:31][CH:32]=[C:33](B(O)O)[CH:34]=2)[N:24]([CH:44]([CH3:46])[CH3:45])[N:23]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:16]([O:15]1[CH2:10][CH2:11][CH2:12][CH:7]([C:6]2[N:5]([CH3:20])[N:4]=[CH:3][C:2]=2[C:33]2[CH:34]=[C:35]3[C:30](=[CH:31][CH:32]=2)[C:29]2[N:39]([CH:40]=[C:27]([C:25]4[N:24]([CH:44]([CH3:45])[CH3:46])[N:23]=[C:22]([CH3:21])[N:26]=4)[N:28]=2)[CH2:38][CH2:37][O:36]3)[CH2:8][NH:9][C:13]1=[O:14])([CH3:19])([CH3:18])[CH3:17]
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참가 물질

6

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HCID 11430Potassium CarbonateHCID 68313095{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}boronic acidHCID 68313245tert-Butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

생성물 1

HCID 178432608HCID 178432608, 화합물수율 50%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate (680 mg, 1.98 mmol) in dioxane (20.0 mL), was added {4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}boronic acid (660 mg, 1.87 mmol), K2CO3 (780 mg, 5.70 mmol), and Pd(dppf)Cl2 (117 mg, 0.19 mmol). The resulting mixture was stirred at 80° C. for 18 h. After concentration, the residue was diluted with EtOAc (20 mL) and washed with brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in petroleum ether to give 1-tert-butyl-5-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)-λ3,3-oxazocan-2-one (540 mg, 50% yield) as a yellow solid. LCMS (ESI) m/z: 573.4 [M+H+].

후처리

  1. concentrationAfter concentration
  2. additionthe residue was diluted with EtOAc (20 mL)
  3. washwashed with brine (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a 0-20% gradient of EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-ef324a77f44e4cc7ba8b2b9c9d19269e
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090628B2

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