Iodine → HCID 178451735, 화합물

HRID 1520017노트

반응식

HRID 1520017 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 178451735HCID 178451735, 화합물수율 79.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-004b6a6db89b4b27be84bae12c2b62d1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073892B2

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