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

HRID 475273노트

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HRID 475273 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 748905826-chloro-1H-indole-5-carbonitrile수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3667633bd8364d6cb417c7ede19dd692
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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