Triacetoxyperiodinane → (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone

HRID 1854490ノート

反応式

HRID 1854490 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH:36]([C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40]3[N:45]([Si:48]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[CH:49]([CH3:51])[CH3:50])[CH:46]=[CH:47][C:39]=23)[OH:37])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40]3[N:45]([Si:48]([CH:52]([CH3:54])[CH3:53])([CH:55]([CH3:57])[CH3:56])[CH:49]([CH3:50])[CH3:51])[CH:46]=[CH:47][C:39]=23)=[O:37])[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 58010130(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol

生成物 1

HCID 58010051(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone収率 25%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dess-Martin periodinane (14.63 g, 34.5 mmol) was added to a solution of (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol (5.89 g, 11.5 mmol) in DCM (120 mL) at about 0° C. and the resulting mixture was stirred for about 16 h while warming to ambient temperature. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous NaHCO3 (150 mL) and EtOAc (200 mL). The organic phase was washed with brine (120 mL) and concentrated under reduced pressure. Purification by silica gel chromatography eluting first with heptane (IL) and then with 1:7 EtOAc:heptane (1 L) yielded (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone (1.45 g, 25%) as a yellow oil: LC/MS (Table 2, Method a) Rt=3.24 min; MS m/z: 511 (M+H)+

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between saturated aqueous NaHCO3 (150 mL) and EtOAc (200 mL)
  3. washThe organic phase was washed with brine (120 mL)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography
  6. washeluting first with heptane (IL)

出典と根拠

ORDレコード
ord-db464d88cc714fb4b246807440dd7c98
出典データセット
uspto-grants-2015_02
特許番号
US08962629B2

反応ノート

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