Potassium tert-butoxide → 6-chloro-1H-indole-5-carbonitrile

HRID 475273ノート

反応式

HRID 475273 の反応式
[NH2:1][C:2]1[C:9]([C:10]#[CH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:12])[CH:3]=1.CC([O-])(C)C.[K+]>C1COCC1>[Cl:12][C:4]1[CH:3]=[C:2]2[C:9]([CH:10]=[CH:11][NH:1]2)=[CH:8][C:5]=1[C:6]#[N:7]

参加物

4

反応物 2

HCID 23665647Potassium tert-butoxideHCID 866947484-Amino-2-chloro-5-ethynylbenzonitrile

生成物 1

HCID 748905826-chloro-1H-indole-5-carbonitrile収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

To a solution of 240 (50 mg, 0.284 mmol) in THF (100 mL) was added t-BuOK (160 mg, 1.42 mmol). The mixture was heated at 75° C. for 3 h during which the color of the reaction mixture changed from yellow to brown. After the mixture was cooled, it was partitioned between EtOAc (200 mL) and H2O (50 mL). The organic layer was separated, washed with brine, dried and concentrated in vacuo to afford 43 mg (86%) of 6-chloro-1H-indole-5-carbonitrile (242) as white solid: 1H NMR (500 MHz, DMSO-d6) (511.80 (s, 1H), 8.21 (s, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 6.61 (d, 1H); MS (ESI) m/z=177.0 [M+1]+.

後処理

  1. temperatureAfter the mixture was cooled
  2. customit was partitioned between EtOAc (200 mL) and H2O (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3667633bd8364d6cb417c7ede19dd692
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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