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Sodium Carbonate → Ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate

HRID 1467302
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HRID 1467302 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[N:4]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[N:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[N:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=3)[N:4]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)=[CH:37][CH:36]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 67984870HCID 67984870, 화합물

생성물 1

HCID 67996877Ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 31275
1,4-Dioxane
용매

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온도
80 °C

실험 절차

To a 5 ml microwave vial equipped with a stir bar was added ethyl 3-bromo-1-trityl-1H-indazole-5-carboxylate (1095.3 mg, 2.142 mmol), pyridine-4-boronic acid pinacol ester (679 mg, 3.21 mmol), sodium carbonate (2142 μl, 4.28 mmol), dioxane (1.07E+04 μl), and PalladiumTetrakis (247 mg, 0.214 mmol). The vial was purged with nitrogen, and was then sealed and heated to 80° C. for 24 h. LCMS taken after 24 hours indicates formation of the desired product. The crude reaction mixture was filtered through a column pre-packed with celite. The combined organics were concentrated under reduced pressure and the material was dry loaded onto a 100 g column. A column was run from 100% hexanes to 100% ethyl acetate. The desired product eluted; fractions were collected and concentrated in vacuo

후처리

  1. customTo a 5 ml microwave vial equipped with a stir bar
  2. customThe vial was purged with nitrogen
  3. customwas then sealed
  4. customThe crude reaction mixture
  5. filtrationwas filtered through a column pre-packed with celite
  6. concentrationThe combined organics were concentrated under reduced pressure
  7. customthe material was dry
  8. washThe desired product eluted
  9. customfractions were collected
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2198061c104b4a368590e5be3d3add7e
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999957B2

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