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Nitrogen → HCID 68471318, 화합물

HRID 506780
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인쇄 미리보기

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HRID 506780 반응식
Br[C:2]1[C:6]2=[N:7][C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=[C:5]2[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[N:29]([S:45]([C:48]3[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=3)(=[O:47])=[O:46])[C:30]([Sn](CCCC)(CCCC)CCCC)=[CH:31][C:24]=12.N#N>C1(C)C=CC=CC=1.[Cu]I.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>[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[N:29]([S:45]([C:48]3[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=3)(=[O:47])=[O:46])[C:30]([C:2]3[C:6]4=[N:7][C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=[C:5]4[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=3)=[CH:31][C:24]=12
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참가 물질

7

반응물 3

HCID 947Nitrogen2회HCID 594326124-Chloro-1-(toluene-4-sulfonyl)-2-tributylstannanyl-1H-pyrrolo[2,3-b]pyridineHCID 68469784t-Butyl 3-bromo-5,6-dimethoxy-pyrrolo[3,2-b]pyridine-1-carboxylate

생성물 1

HCID 68471318HCID 68471318, 화합물수율 68.6%

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 1140Toluene용매

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온도
120 °C

실험 절차

Bubble a solution of dimethoxyazaindole 11 (0.25 g, 0.70 mmol) and azaindole 26 (0.458 g, 0.77 mmol) in toluene (15 mL) with N2 for 15 min, then add CuI (14 mg, 0.07 mmol) and Pd(PPh3)4 (81 mg, 0.07 mmol) and agitate the mixture with the stream of N2 for 0.5 h, then heat at 120° C. under N2 for 20 h. Purification of the reaction mixture on SiO2 (flash chromatography, 40 g cartridge, elution with EtOAc at 10-30%/heptane) gives bisazaindole 27 (0.28 g, 68%) as a white solid: 1H NMR (CDCl3) δ 8.29 (d, 1H, J=5.4 Hz), 7.86 (s apparent overlapping d, 3H), 7.15 (m, 4H), 6.94 (s, 1H), 3.97 (s, 6H), 2.32 (s, 3H), 1.71 (s, 9H), TLC (EtOAc at 40%/heptane) Rf=0.40.

후처리

  1. customPurification of the reaction mixture on SiO2 (flash chromatography, 40 g cartridge, elution with EtOAc at 10-30%/heptane)

출처 및 근거

ORD 기록
ord-42bc05642b8c4b2fadf73d196dd1e9ef
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786114B2

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