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Cyano-borohydride → (1RS,2RS)-1-[6-chloro-1-(4-fluorophenyl)indazol-5-yl]oxy-1-(4-fluorophenyl)propan-2-amine

HRID 13117
ノート
印刷プレビュー

反応式

HRID 13117 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[O:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:20]([CH3:22])=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:36]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[O:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH:20]([NH2:36])[CH3:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 498716Cyano-borohydrideHCID 517165Ammonium AcetateHCID 593396341-{[6-Chloro-1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(4-fluorophenyl)acetone

生成物 1

HCID 59786589(1RS,2RS)-1-[6-chloro-1-(4-fluorophenyl)indazol-5-yl]oxy-1-(4-fluorophenyl)propan-2-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
140 °C

実験手順

1-{[6-Chloro-1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(4-fluorophenyl)acetone (500 mg, 1.21 mmol), ammonium acetate (934 mg, 12.11) and cyanoborohydride on polymer support (1.82 g, 3.63 mmol) were mixed in methanol (3 ml) and heated in micro at 140° C. for 10 min. The mixture was concentrated and treated with NaHCO3 and DCM. The organic phase was concentrated and the crude product was purified by flash chromatography (EtOAc/heptane followed by EtOAc/methanol). The diasteromers were separated on preparative HPLC (Kromasil column, water buffered with 2 g NH4OAc/l, pH set to 5.5 with HOAc, and MeCN, 25%-75%) to give the syn-isomer (1RS,2RS)-1-[6-chloro-1-(4-fluorophenyl)indazol-5-yl]oxy-1-(4-fluorophenyl)propan-2-amine (98a-rac-1) as first eluated isomer (assignment by 1H-NMR).

後処理

  1. concentrationThe mixture was concentrated
  2. additiontreated with NaHCO3 and DCM
  3. concentrationThe organic phase was concentrated
  4. customthe crude product was purified by flash chromatography (EtOAc/heptane followed by EtOAc/methanol)
  5. customThe diasteromers were separated on preparative HPLC (Kromasil column, water

出典と根拠

ORDレコード
ord-26312b9658f04086b3dc185c41eaca8c
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728030B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート