Triethylamine → 4-(5-Bromopyridin-2-yl)-1,4-diazepan-2-one

HRID 2207341ノート

反応式

HRID 2207341 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[CH:6][CH:7]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][C:10]1=[O:16].C(N(CC)CC)C>CN(C)C(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:12]2[CH2:13][CH2:14][CH2:15][NH:9][C:10](=[O:16])[CH2:11]2)=[N:4][CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 134285321,4-Diazepan-2-one

生成物 1

HCID 647225474-(5-Bromopyridin-2-yl)-1,4-diazepan-2-one

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of 3-bromo-6-fluoropyridine (315 mg, 1.79 mmol), 1,4-diazepan-2-one (200 mg, 1.75 mmol), and triethylamine (0.269 ml, 1.93 mmol) in N,N-dimethylacetamide (3 mL) was irradiated in a microwave reactor for twenty minutes at 220° C. The reaction mixture was diluted with ethyl acetate (35 mL) and then washed with saturated aqueous sodium bicarbonate (15 mL), water (3×10 mL), and brine (15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0.5-8.5% methanol/dichloromethane) to afford 4-(5-bromopyridin-2-yl)-1,4-diazepan-2-one. MS ESI calc'd. for C10H13BrN3O [M+H]+ 270 and 272. found 270 and 272. 1H NMR (500 MHz, DMSO-d6): δ 8.14 (d, J=2.4 Hz, 1H), 7.68 (dd, J=9.1, 2.7 Hz, 1H), 7.48 (m, 1H), 6.70 (d, J=9.1 Hz, 1H), 4.11 (s, 2H), 3.85 (s, 2H), 3.18 (m, 2H), 1.62 (m, 2H).

後処理

  1. washwashed with saturated aqueous sodium bicarbonate (15 mL), water (3×10 mL), and brine (15 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (0.5-8.5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-826abac64754418ab8373702dfe5b108
出典データセット
uspto-grants-2016_06
特許番号
US09376418B2

反応ノート

読み込み中…