Potassium Iodide → Tyclopyrazoflor

HRID 55744

반응식

HRID 55744 반응식
[H-].[Na+].[Cl:3][C:4]1[C:8]([NH:9][C:10](=[O:20])[CH2:11][CH2:12][S:13][CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:7][N:6]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:5]=1.[CH2:27](Br)[CH3:28].[I-].[K+]>S1(CCCC1)(=O)=O>[Cl:3][C:4]1[C:8]([N:9]([CH2:27][CH3:28])[C:10](=[O:20])[CH2:11][CH2:12][S:13][CH2:14][CH2:15][C:16]([F:18])([F:17])[F:19])=[CH:7][N:6]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:5]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 86700584N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((3,3,3-trifluoropropyl)thio)propanamide

생성물 1

HCID 86700627Tyclopyrazoflor

시약·촉매·용매 1

HCID 31347Sulfolane용매2회

실험 절차

To 3-neck round bottomed flask (50 mL) was added sodium hydride (60% in oil, 0.130 g, 3.28 mmol) and sulfolane (16 mL). The gray suspension was stirred for 5 minutes then N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((3,3,3-trifluoropropyl)thio)propanamide (1.20 g, 3.16 mmol) dissolved in sulfolane (25 mL) was slowly added dropwise over 5 minutes. The mixture became a light gray suspension after 3 minutes and was allowed to stir for 5 minutes after which time ethyl bromide (0.800 mL, 10.7 mmol) and potassium iodide (0.120 g, 0.720 mmol) were added sequentially. The cloudy suspension was then allowed to stir at room temperature. The reaction was quenched after 6 hours by being poured drop-wise into cooled ammonium formate/acetonitrile solution (30 mL). The resulting orange colored solution was stirred and tetrahydrofuran (40 mL) was added. The mixture was assayed, using octanophenone as a standard, and found to contain (1.09 g, 85%) of the desired product with a selectivity versus the retro-Michael-like decomposition product of 97:3.

후처리

  1. additionwas slowly added dropwise over 5 minutes
  2. customafter 3 minutes
  3. additionwere added sequentially
  4. stirringto stir at room temperature
  5. customThe reaction was quenched after 6 hours
  6. additionby being poured drop-wise
  7. temperatureinto cooled ammonium formate/acetonitrile solution (30 mL)
  8. stirringThe resulting orange colored solution was stirred
  9. additiontetrahydrofuran (40 mL) was added

출처 및 근거

ORD 기록
ord-8c178e7cd78948a2aefcc4ac48964a1b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433215B2

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