Sodium borohydride → HCID 90046925, 화합물

HRID 1504997노트

반응식

HRID 1504997 반응식
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20](=[O:22])[CH3:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(Cl)Cl>[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([OH:22])[CH3:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:6])=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 90046976HCID 90046976, 화합물

생성물 1

HCID 90046925HCID 90046925, 화합물수율 98.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-one (100 mg, 0.281 mmol) in MeOH (2810 μl) was added NaBH4 (13.29 mg, 0.351 mmol) at rt. This was stirred at rt for 20 min. Removed solvent in vacuo. Redissolved in DCM and quenched with sat aq NH4Cl. Separated and extracted twice more with DCM. Washed combined organics with brine, then dried on MgSO4, filtered and concentrated providing 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-ol (98.8 mg, 0.276 mmol, 98% yield) as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (d, J=6.06 Hz, 3H) 1.33 (s, 9H) 4.00-4.20 (m, 3H) 4.81 (d, J=4.29 Hz, 1H) 7.74 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.65 (s, 1H) 8.94 (d, J=4.80 Hz, 1H). MS: m/z: 358.1 [M+H]+.

후처리

  1. customquenched with sat aq NH4Cl
  2. customSeparated
  3. extractionextracted twice more with DCM
  4. washWashed
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c928694d22ac49b184c82ab3e5c329d5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216965B2

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