Aniline → HCID 89782082、化合物

HRID 1056002

反応式

HRID 1056002 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15](Cl)[C:16]([CH3:22])=[N:17]2.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCOCC1.CCOC(C)=O>[Br:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]([CH3:22])=[N:17]2

参加物

6

反応物 3

HCID 6115AnilineHCID 2733832Lithium HexamethyldisilazideHCID 894288875-Bromo-3-chloro-2-methylquinoxaline

生成物 1

HCID 89782082HCID 89782082、化合物収率 71%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

LHMDS (1.0M in THF; 14.37 ml, 14.37 mmol) was added to a solution of 5-bromo-3-chloro-2-methylquinoxaline (126e, 0.74 g, 2.87 mmol) and aniline (1.309 ml, 14.37 mmol, Alfa Aesar, Ward Hill, Mass.) in dioxane (28.7 ml) at RT, and the resulting mixture was stirred at RT for 30 min. The mixture was diluted with EtOAc (200 ml), added to a separatory funnel, and washed with saturated aq. NH4Cl (2×150 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica gel (100% hexanes to 20% EtOAc/hexanes) provided 8-bromo-3-methyl-N-phenylquinoxalin-2-amine (183a, 71% yield) as a brown oil. MS (ESI, pos. ion) m/z: 314.2/316.2 (M+1).

後処理

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NH4Cl (2×150 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel (100% hexanes to 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-2e342e456a10458b950e04da86d5375f
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

関連ノート

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