Iodine → HCID 178451735、化合物

HRID 1520017ノート

反応式

HRID 1520017 の反応式
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[CH:9][CH:10]=2)[CH:5]=[N:4]1.[I:25]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[I:25][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH:7]=2)[NH:3][N:4]=1

参加物

6

反応物 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 49760224tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate

生成物 1

HCID 178451735HCID 178451735、化合物収率 79.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

KOH (141.5 mg; 2.52 mmol; 3.8 eq.) pellets were added in small portion during 10 min to a solution of tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate (200 mg; 0.66 mmol; 1.0 eq.) and iodine (0.34 g; 1.33 mmol; 2.0 eq.) in dry DMF (6 mL). The reaction mixture was stirred O/N at RT. It was then poured into a saturated solution of Na2S2O3 (100 mL) and extracted three times with ether. Combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow foam (225 mg, 79%). 1H NMR (300 MHz, DMSO-d6) δ 13.41 (brs, 1H), 7.48 (d, J=8.6 Hz, 1H), 7.35 (dd, J=8.7, 1.3 Hz, 1H), 7.20 (s, 1H), 4.26-3.94 (m, 2H), 2.93-2.74 (m, 3H), 1.99-1.70 (m, 2H), 1.67-1.47 (m, 2H), 1.42 (s, 9H). HPLC (Condition A): Rt 5.10 min (purity 100%).

後処理

  1. extractionextracted three times with ether
  2. washCombined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-004b6a6db89b4b27be84bae12c2b62d1
出典データセット
uspto-grants-2015_07
特許番号
US09073892B2

反応ノート

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