3-Butyn-2-amine, 2-methyl- → 1,1-Dimethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-prop-2-ynylamine

HRID 1175139노트

반응식

HRID 1175139 반응식
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)[O:3]1.[CH3:17][C:18]([NH2:22])([CH3:21])[C:19]#[CH:20]>CN(C=O)C.CCN(CC)CC.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>[CH3:17][C:18]([NH2:22])([CH3:21])[C:19]#[C:20][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5]2)=[CH:10][CH:11]=1

참가 물질

5

반응물 2

HCID 763193-Butyn-2-amine, 2-methyl-HCID 107553762-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 595586551,1-Dimethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-prop-2-ynylamine

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 22056947triethylamine N,N-dimethylformamide용매

실험 절차

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene (J. Organomet. Chem. 2006, 691 (26), 5725) (200 mg; 0.71 mmol) 1,1-dimethyl-prop-2-ynylamine (350 mg; 4.25 mmol) Pd(PPh3)2Cl2 (99 mg; 0.14 mmol) and Cul (27 mg; 0.14 mmol) are dissolved in DMF/NEt3 (3.5 ml/1.5 ml) and microwaved at 100° C. for 20 minutes. The reaction mixture is evaporated and purified via chromatography (SiO2; TBME/MeOH/M/NH3conc 95:5:0.8) to yield the title compound as yellowish crystals. H-NMR (400 Hz; DMSO-d6): 7.64 (d, 2H); 7.38 (d, 2H); 2.08 (bs, 2H); 1.39 (s, 6H); 1.31 (s, 12H). MS (m/z) ES+: 285 (MH+).

후처리

  1. custommicrowaved at 100° C. for 20 minutes
  2. customThe reaction mixture is evaporated
  3. custompurified via chromatography (SiO2; TBME/MeOH/M/NH3conc 95:5:0.8)

출처 및 근거

ORD 기록
ord-7255a7a0ec8a449a8c09b52de1f19d33
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838674B2

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