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Ammonium Hydroxide → 4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 1188360
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HRID 1188360 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C(C)(C)C)=[C:4]([C:15]#[C:16][Si](C)(C)C)[C:3]=1[C:21]([F:24])([F:23])[F:22].[C:25]([Cu])#[N:26].[OH-].[NH4+]>CN1C(=O)CCC1>[F:24][C:21]([F:22])([F:23])[C:3]1[C:2]([C:25]#[N:26])=[CH:7][CH:6]=[C:5]2[C:4]=1[CH:15]=[CH:16][NH:8]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 57800198HCID 57800198, 화합물HCID 178418546HCID 178418546, 화합물

생성물 1

HCID 674054494-(trifluoromethyl)-1H-indole-5-carbonitrile

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
250 °C

실험 절차

An NMP solution (15 mL) of N-{4-chloro-3-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]phenyl}-2,2-dimethylpropanamide (1.04 g, 2.77 mmol) was treated with CuCN (1.04 g, 11.01 mmol) and the resulting mixture was heated at 250° C. in a microwave for 5.5 h. The dark brown reaction mixture was poured into crushed ice (250 mL) containing conc. ammonium hydroxide (30 mL). The resulting slurry was filtered and rinsed with Et2O. The filtrate was diluted with Et2O (50 mL) and partitioned. The aqueous portion was extracted with Et2O (2×25 mL). The combined organic portions were washed with H2O (25 mL) and brine (25 mL). Drying (Na2SO4) and filtration were followed by concentration to a brown/yellow solid (0.723 g) that was used for the next reaction without further purification.

후처리

  1. additionThe dark brown reaction mixture was poured
  2. filtrationThe resulting slurry was filtered
  3. washrinsed with Et2O
  4. additionThe filtrate was diluted with Et2O (50 mL)
  5. custompartitioned
  6. extractionThe aqueous portion was extracted with Et2O (2×25 mL)
  7. washThe combined organic portions were washed with H2O (25 mL) and brine (25 mL)
  8. customDrying
  9. filtration(Na2SO4) and filtration
  10. concentrationwere followed by concentration to a brown/yellow solid (0.723 g) that
  11. customwas used for the next reaction without further purification

출처 및 근거

ORD 기록
ord-15825b1769c84cbfbfcc6c2491abd412
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673948B2

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