Tetrabutylammonium Fluoride → HCID 59852950、化合物

HRID 2237305ノート

反応式

HRID 2237305 の反応式
C[Si](C)(C)[C:3]#[C:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:4]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:7][CH:6]=1)#[CH:3]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 59853054Carbamic acid, [6-[(trimethylsilyl)ethynyl]-3-pyridinyl]-, 1,1-dimethylethyl ester

生成物 1

HCID 59852950HCID 59852950、化合物収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl 6-(2-(trimethylsilyl)ethynyl)pyridin-3-ylcarbamate (62 mg, 0.21 mmol) in THF (5 mL) was cooled to −15° C. and treated with 1.0 M tetrabutylammonium fluoride (Aldrich, 0.25 mL, 0.25 mmol) and stirred for 40 min. The mixture was concentrated in vacuo and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The EtOAc phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (45 mg, 100%) as an off-white solid. 1H NMR (DMSO-d6) δ 9.78 (s, 1H), 8.58 (d, 1H, J=2.5 Hz), 7.92-7.84 (m, 1H), 7.46 (d, 1H, J=8.6 Hz), 4.17 (s, 1H), 1.47 (s, 9H); MS(ESI+): m/z 219.20 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. washThe EtOAc phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d98b6f5c01fa4ad9821bbfe61cc32236
出典データセット
uspto-grants-2010_05
特許番号
US07714138B2

反応ノート

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