Tetrabutylammonium Fluoride → HCID 86670548、化合物

HRID 874715ノート

反応式

HRID 874715 の反応式
[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

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67167406HCID 67167406、化合物

生成物 1

HCID 86670548HCID 86670548、化合物収率 87.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-ac78428e0f6f45f586177a4cb9f04ac3
出典データセット
uspto-grants-2015_03
特許番号
US08980926B2

反応ノート

読み込み中…