Cyanogen Bromide → 5-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine

HRID 627993ノート

反応式

HRID 627993 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[N:24][NH2:25])[NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:23])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1.[N:27]#[C:28]Br>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]4[N:16]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[Cl:23])[C:28]([NH2:27])=[N:25][N:24]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1

参加物

4

反応物 2

HCID 10476Cyanogen BromideHCID 178514378HCID 178514378、化合物

生成物 1

HCID 579002025-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine収率 21%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
45 °C

実験手順

A solution of crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide (195, 0.434) in methanol (5 mL) was treated with a solution of cyanogen bromide (115 mg, 1.1 mmol) in methanol (1 mL) at room temperature. The reaction vessel was sealed and heated at 45° C. for 2 h, cooled to room temperature, quenched upon addition of saturated sodium bicarbonate and extracted with ethylacetate. The combined organics were dried over sodium sulfate and concentrated and the residue purified by flash column chromatography (1-10% MeOH in methylene chloride to give 287 (43 mg, 21% yield). MS (ESI): 475.0

後処理

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temperature
  3. customquenched upon addition of saturated sodium bicarbonate
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue purified by flash column chromatography (1-10% MeOH in methylene chloride

出典と根拠

ORDレコード
ord-a2240e7550c3435483df56c6ea7716d5
出典データセット
uspto-grants-2016_04
特許番号
US09309265B2

反応ノート

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