Tetrabutylammonium Fluoride → HCID 86670548, 화합물

HRID 874715노트

반응식

HRID 874715 반응식
[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]3)=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]#[C:26][Si](C)(C)C)[CH:8]=2)[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]3)=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]#[CH:26])[CH:8]=2)[N:3]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 67167406HCID 67167406, 화합물

생성물 1

HCID 86670548HCID 86670548, 화합물수율 87.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-amino-3-{4-[3-(trifluoromethyl)diazirin-3-yl]phenyl}-5-[2-(trimethylsilyl)ethynyl]indol-3-ol (30.5 mg, 0.07 mmol, 1 eq.) was dissolved in THF (5 mL), and 1 M TBAF in THF (0.078 mL, 0.08 mmol, 1.1 eq.) was added. The reaction was stirred at room temperature for 10 minutes. Solvents were then evaporated, and the residue was purified by silica column (DCM/MeOH, 39:1→19:1→9:1→4:1), resulting in 21.8 mg (86%) of the title compound as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 7.45 (d, J=8.5, 2H, Ar—H), 7.33 (dd, J=1.5, 8.0, 1H, Ar—H), 7.23 (d, J=8.2, 2H, Ar—H), 7.10-6.94 (m, 2H, Ar—H). 13C NMR (126 MHz, CD3OD) δ 180.61 (CNH2), 156.96 (C—Ar), 144.65 (C—Ar), 140.97 (C—Ar), 135.30 (C—Ar), 129.59 (C—Ar), 127.92 (d, J=0.90, C—Ar), 127.76 (C—Ar), 127.02 (C—Ar), 123.73 (q, J=273.90, CF3), 117.13 (C—Ar), 116.69 (C—Ar), 84.96 (CCH), 84.23 (Ar—COH), 77.31 (CCH), 29.56 (q, J=40.35, CN2). Exact Mass, 356.09. 354.7202 [M−H]−, 356.7268 [M+H]+.

후처리

  1. customSolvents were then evaporated
  2. customthe residue was purified by silica column (DCM/MeOH, 39:1→19:1→9:1→4:1)

출처 및 근거

ORD 기록
ord-ac78428e0f6f45f586177a4cb9f04ac3
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980926B2

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