Triethylamine → tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 45579

반응식

HRID 45579 반응식
C[Si]([C:5]#[CH:6])(C)C.C(N(CC)CC)C.I[C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=3)[CH:22]=2)[N:17]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:16]=1.[CH2:37]([N:44]=[N+:45]=[N-:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:37]([N:44]1[CH:6]=[C:5]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[CH:22]=3)[N:17]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:16]=2)[N:46]=[N:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 12152Benzyl azideHCID 66111TrimethylsilylacetyleneHCID 58217086Tert-butyl 3-iodo-5-(1-methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine-1-carboxylate

생성물 1

HCID 66778317tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

3.4 0.09 ml (0.63 mmol) of trimethylsilylacetylene and 0.12 ml (0.84 mmol) of triethylamine are added successively to a suspension, kept under argon, of 6 mg (0.009 mmol) of bis(triphenylphosphine)palladium dichloride, 3 mg (0.016 mmol) of copper(I) iodide and 178 mg (0.42 mmol) of tert-butyl 3-iodo-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate in 2 ml of THF, and the mixture is stirred at room temperature for one hour under argon. Then, for the removal of excess trimethylsilylacetylene, argon is passed through the reaction mixture for 5 minutes. 0.45 ml (0.45 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added, and the reaction mixture is stirred at room temperature for 30 minutes. A solution of 58 mg (0.42 mmol) of benzyl azide in 2 ml of methanol is then added, and the reaction mixture is stirred at room temperature for 48 hours. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent, giving tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate as colourless crystals; ESI 456.

후처리

  1. customThen, for the removal of excess trimethylsilylacetylene, argon
  2. waitis passed through the reaction mixture for 5 minutes
  3. addition0.45 ml (0.45 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added
  4. stirringthe reaction mixture is stirred at room temperature for 30 minutes
  5. stirringthe reaction mixture is stirred at room temperature for 48 hours
  6. customchromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-45aa048f23b84ad886f726280d507db4
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541584B2

연결된 노트

불러오는 중…