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Triethylamine → 4-Methyl-N-(3-morpholin-4-yl-propyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

HRID 2216214
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HRID 2216214 반응식
I[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:5]([NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:6].C(N(CC)CC)C.[CH3:28][C:29]1([CH3:36])[C:33]([CH3:35])([CH3:34])[O:32][BH:31][O:30]1>O1CCOCC1.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>[CH3:20][C:19]1[CH:18]=[CH:17][C:4]([C:5]([NH:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:6])=[CH:3][C:2]=1[B:31]1[O:32][C:33]([CH3:35])([CH3:34])[C:29]([CH3:36])([CH3:28])[O:30]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 21886113HCID 21886113, 화합물

생성물 1

HCID 218861494-Methyl-N-(3-morpholin-4-yl-propyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 31275
1,4-Dioxane
용매

실험 절차

The procedure used in Example 3: step b was followed using 3-iodo-4-methyl-N-(3-morpholin-4-yl-propyl)-benzamide ((Example 301: step a) 695 mg, 1.79 mmol), PdCl2(PPh3)2 (63 mg, 0.09 mmol), triethylamine (1.25 mL, 9.4 mmol), and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.91 mL, 6.4 mmol) in dioxane (5 mL). Analogous aqueous workup and purification by SiO2 flash column chromatography (0–10% MeOH in DCM) yielded the title compound contaminated with the product resulting from halide reduction (653 mg, 94%). The material was used without further purification.

후처리

  1. customAnalogous aqueous workup and purification by SiO2 flash column chromatography (0–10% MeOH in DCM)

출처 및 근거

ORD 기록
ord-c0ad5057b2ac49b099c2dc8a8e9f3bad
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07109354B2

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