Water → (S)-4-(5,7-dibromo-2,3-dihydro-1H-indol-1-yl)-1-[1-(methoxymethyl)-3-methoxypropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine

HRID 1060620노트

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HRID 1060620 반응식
ClC1C2N=NN([C@H](COC)CCOC)C=2C=C(C)N=1.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([Br:30])[CH:29]=1)[N:26]([C:31]1[C:36]3[N:37]=[N:38][N:39]([C@H:40]([CH2:45][O:46][CH3:47])[CH2:41][CH2:42][O:43][CH3:44])[C:35]=3[CH:34]=[C:33]([CH3:48])[N:32]=1)[CH2:25][CH2:24]2.BrC1C=C2C(=C(Br)C=1)NCC2.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O>C1COCC1>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([Br:30])[CH:29]=1)[N:26]([C:31]1[C:36]3[N:37]=[N:38][N:39]([C@H:40]([CH2:45][O:46][CH3:47])[CH2:41][CH2:42][O:43][CH3:44])[C:35]=3[CH:34]=[C:33]([CH3:48])[N:32]=1)[CH2:25][CH2:24]2

참가 물질

6

반응물 4

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18629224HCID 18629224, 화합물HCID 86583721(S)-4-(5,7-Dibromo-2,3-dihydro-1H-indol-1-yl)-1-[1-(methoxymethyl)-3-methoxypropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine (S)-4-chloro-1-(1-methoxymethyl-3-methoxypropyl)-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine

생성물 1

HCID 9936650(S)-4-(5,7-dibromo-2,3-dihydro-1H-indol-1-yl)-1-[1-(methoxymethyl)-3-methoxypropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine수율 85.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

Part J:(S)-4-(5,7-Dibromo-2,3-dihydro-1H-indol-1-yl)-1-[1-(methoxymethyl)-3-methoxypropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine (S)-4-chloro-1-(1-methoxymethyl-3-methoxypropyl)-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine (0.72 g, 2.54 mmol) and 5,7-dibromoindoline (0.72 g, 2.60 mmol) were dissolved in anhydrous THF (6 mL) and cooled in an ice bath. To that a 1 M solution of NaHMDS in THF (3.0 mL, 3.0 mmol) was added and the reaction was stirred for 20 min, allowed to warm to 25° C. and stirred for 3 h. Then water (30 mL) was added and the mixture was extracted twice with EtOAc (80 and 40 mL). The combined organic extracts was washed with brine (30 mL) dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 40% EtOAc/hexanes as eluent to give the product (1.14 g, 85% yield).

후처리

  1. temperaturecooled in an ice bath
  2. stirringstirred for 3 h
  3. extractionthe mixture was extracted twice with EtOAc (80 and 40 mL)
  4. washThe combined organic extracts was washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customThe residue was chromatographed on silica gel using 40% EtOAc/hexanes as eluent

출처 및 근거

ORD 기록
ord-23d5e2dcaf2541ef87b765a4ed809fbb
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525056B2

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