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 1517620ノート

反応式

HRID 1517620 の反応式
[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

参加物

7

反応物 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]

生成物 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]収率 56.6%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4649680252194f979012a7a1c5210a16
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

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