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Sodium Carbonate → 1-Methyl-2-[5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-1H-indole

HRID 2305102
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HRID 2305102 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1B(O)O.Br[C:15]1[CH:16]=[C:17]([O:21][CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[CH3:28])[CH:18]=[N:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:15]1[CH:16]=[C:17]([O:21][CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[CH3:28])[CH:18]=[N:19][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridineHCID 22733820(1-Methyl-1H-indol-2-yl)boronic acid

생성물 1

HCID 443723681-Methyl-2-[5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-1H-indole

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of the compound from step 36a and 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (270 mg, 1.0 mmol) in toluene (5.0 mL) was added Pd(0) (25 mg) and Na2CO3 (1 mL of a 2 M solution), and the mixture was heated at reflux for 60 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on silica gel to afford 105 mg of the title compound. MS (CI/NH3) m/z 322 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.80 (m, 3H), 2.05 (m, 1H), 2.32 (m, 1H), 2.50 (s, 3H), 2.70 (m, 1H), 3.13 (m, 1H), 3.78 (s, 3H), 4.04 (m, 2H), 6.62 (s, 1H), 7.18 (m, 2H), 7.35 (m, 2H), 7.66 (m, 1H), 8.38 (m, 2H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 60 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-e63bf781e41e49b5a62eac11436a0a06
출처 데이터셋
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06437138B1

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