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 1060620ノート

反応式

HRID 1060620 の反応式
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

参加物

6

反応物 4

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18629224HCID 18629224、化合物HCID 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

生成物 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]pyridine収率 85.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-23d5e2dcaf2541ef87b765a4ed809fbb
出典データセット
uspto-grants-2003_02
特許番号
US06525056B2

反応ノート

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