Sodium Carbonate → HCID 178424919, 화합물

HRID 1392682노트

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HRID 1392682 반응식
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[CH3:20])=[C:4]([O:21][CH:22]([CH3:24])[CH3:23])[CH:3]=1.[CH:25]([C:28]1[C:36]2[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][C:31]=2[NH:30][N:29]=1)([CH3:27])[CH3:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH:22]([O:21][C:4]1[C:5]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[CH3:20])=[C:6]([CH3:8])[N:7]=[C:2]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:36]=2[C:28]([CH:25]([CH3:27])[CH3:26])=[N:29][NH:30]3)[CH:3]=1)([CH3:24])[CH3:23]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 865939916-Chloro-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridineHCID 178440403HCID 178440403, 화합물

생성물 1

HCID 178424919HCID 178424919, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 6-chloro-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridine (185 mg, 0.53 mmol), 3-isopropyl-1H-indazole-4-boronic acid (109 mg, 0.53 mmol), Pd(PPh3)4 (31 mg, 0.027 mmol), and Na2CO3 (169 mg, 1.6 mmol) in dioxane (8 mL) and water (2 mL) is heated for 24 hours at 100° C. The mixture is poured into water and extracted with EtOAc. The combined extract are dried (Na2SO4) and concentrated in vacuo. The residue is purified by flash chromatography (elution with MeOH/CH2Cl2 1:10) to yield 4-[4-isopropoxy-5-(5-isopropyl-2-methyl-phenyoxymethyl)-6-methyl-pyridin-2-yl]-3-isopropyl-1H-indazole. 1H NMR (CDCl3) 9.95 (br s, 1H), 7.45 (d, 1H), 7.39 (t, 1H), 7.13 (d, 1H), 7.09 (d, 1H), 6.92 (m, 2H), 6.78 (d, 1H), 5.20 (s, 2H), 4.68 (m, 1H), 3.19 (m, 1H), 2.88 (m, 1H), 2.64 (s, 3H), 2.20 (s, 3H), 1.99 (d, 6H), 1.24 (d, 6H), 1.11 (d, 6H). LCMS (m/z): 472.63 (MH)+

후처리

  1. extractionextracted with EtOAc
  2. extractionThe combined extract
  3. dry with materialare dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (elution with MeOH/CH2Cl2 1:10)

출처 및 근거

ORD 기록
ord-271cd93941e04b1c9a808274e44baec2
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342115B2

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