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Potassium Carbonate → HCID 67959919, 화합물

HRID 1529451
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인쇄 미리보기

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HRID 1529451 반응식
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:5]=[C:4]([S:18]([CH3:21])(=[O:20])=[O:19])[N:3]=1.[Br:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:27]=[C:26]2B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.O.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>[Br:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:27]=[C:26]2[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:5]=[C:4]([S:18]([CH3:21])(=[O:20])=[O:19])[N:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 53217221tert-Butyl 5-bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylateHCID 59312818HCID 59312818, 화합물

생성물 1

HCID 67959919HCID 67959919, 화합물수율 41.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
100 °C

실험 절차

A glass microwave reaction vessel was charged with 4-chloro-6-(4-methoxybenzyloxy)-2-(methylsulfonyl)pyrimidine (600 mg, 1.825 mmol) and tert-butyl 5-bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (770 mg, 1.825 mmol) in p-dioxane/H2O (4:1, 6 mL) followed by Pd(PPh3)4 (105 mg, 0.091 mmol) and potassium carbonate (220 μL, 3.65 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 30 min. The mixture was diluted with water and extracted with DCM. The combined organic layers were dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 10-25% EtOAc in Hexanes) to give tert-butyl 5-bromo-3-(6-(4-methoxybenzyloxy)-2-(methylsulfonyl)pyrimidin-4-yl)-1H-indole-1-carboxylate (445 mg, 0.756 mmol, 41.4% yield) as a half solid. MS (ESI, pos. ion) m/z: 587.8 (M+1).

후처리

  1. customA glass microwave reaction vessel
  2. extractionextracted with DCM
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 10-25% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-3159ab1eca904ec3bea4681baafad83d
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090593B2

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