Sodium triacetoxyborohydride → 2-chloro-1'-[[1-(3-chloro-2-pyridyl)-3-methyl-pyrazol-4-yl]methyl]-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]

HRID 1517620노트

반응식

HRID 1517620 반응식
[Cl:1][C:2]1[S:17][C:5]2[C:6]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[O:7][CH2:8][C:9]([F:11])([F:10])[C:4]=2[CH:3]=1.[Cl:18][C:19]1[C:20]([N:25]2[CH:29]=[C:28]([CH:30]=O)[C:27]([CH3:32])=[N:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.ClCCl>[Cl:1][C:2]1[S:17][C:5]2[C:6]3([O:7][CH2:8][C:9]([F:11])([F:10])[C:4]=2[CH:3]=1)[CH2:12][CH2:13][N:14]([CH2:30][C:28]1[C:27]([CH3:32])=[N:26][N:25]([C:20]2[C:19]([Cl:18])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:29]=1)[CH2:15][CH2:16]3

참가 물질

7

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 582685431-(3-Chloro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehydeHCID 582685982'-Chloro-4',4'-difluoro-4',5'-dihydrospiro[piperidine-4,7'-[7H]thieno[2,3-c]pyran]

생성물 1

HCID 582685742-chloro-1'-[[1-(3-chloro-2-pyridyl)-3-methyl-pyrazol-4-yl]methyl]-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]수율 56.6%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2′-chloro-4′,4′-difluoro-4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] (0.2 g, 0.71 mmol) in 1,2-dichloroethane (5 mL) are added 1-(3-chloro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde (0.19 g, 0.86 mmol) and a few drops of acetic acid. The reaction mixture is stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.315 g, 1.43 mmol) is added and stirred at room temperature for 14 hours. After completion, the reaction mixture is diluted with dichloromethane and washed with saturated sodium bicarbonate solution and brine. The organic phase is dried over sodium sulfate and concentrated in vacuo. The crude mixture is purified by HPLC to yield 0.195 g (56%) of 2-chloro-1′-[[1-(3-chloro-2-pyridyl)-3-methyl-pyrazol-4-yl]methyl]-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine]. MS (m/z): 485 (M+1).

후처리

  1. stirringstirred at room temperature for 14 hours
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture is purified by HPLC

출처 및 근거

ORD 기록
ord-4649680252194f979012a7a1c5210a16
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

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