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Methyl N-(triethylammoniosulfonyl)carbamate → 2-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile

HRID 2117989
ノート
印刷プレビュー

反応式

HRID 2117989 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:26](=[CH:27][CH:28]=1)[C:12]1[NH:13][C:14]([C:16]3[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])=[N:15][C:11]=1[C:10]1[CH:9]=[CH:8][C:7]([C:29]#[C:30][C:31](O)([CH3:33])[CH3:32])=[CH:6][C:5]2=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:28]=[CH:27][C:26]2[C:12]3[N:13]=[C:14]([C:16]4[C:17]([C:18]#[N:19])=[CH:20][CH:21]=[CH:22][C:23]=4[C:24]#[N:25])[NH:15][C:11]=3[C:10]3[C:5](=[CH:6][C:7]([C:29]#[C:30][C:31]([CH3:33])=[CH2:32])=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 1784590322-(6-chloro-9-(3-hydroxy-3-methylbut-1-ynyl)-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile

生成物 1

HCID 866148722-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile収率 78.2%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

To a stirred suspension of 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile from Example 40 (120 mg, 0.26 mmol) in benzene (4 mL) was added Burgess Reagent (70 mg, 0.29 mmol) and refluxed for 2 hours under N2. The resulting reaction mixture was diluted with EtOAc (20 mL). This EtOAc solution washed with water, brine and dried over MgSO4. After removing the drying agent via filtration, the organic solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with 50/50 EtOAc/hexane) to yield 90 mg of 2-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile as a yellow solid.

後処理

  1. temperaturerefluxed for 2 hours under N2
  2. customThe resulting reaction mixture
  3. washThis EtOAc solution washed with water, brine
  4. dry with materialdried over MgSO4
  5. customAfter removing the drying agent
  6. filtrationvia filtration
  7. concentrationthe organic solution was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluted with 50/50 EtOAc/hexane)

出典と根拠

ORDレコード
ord-ffd8789965be40689a6e6ac2799cabad
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07442716B2

反応ノート

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