Benzyl Bromide → 2-(1-Benzylpiperidin-4-yloxy)-6-bromobenzo[d]thiazole

HRID 1429533노트

반응식

HRID 1429533 반응식
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[S:8][C:4]=2[CH:3]=1.CCN(CC)CC.Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH2:26]([N:13]1[CH2:12][CH2:11][CH:10]([O:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([Br:1])[CH:17]=[CH:16][C:5]=3[N:6]=2)[CH2:15][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 674668246-Bromo-2-(piperidin-4-yloxy)-benzothiazole

생성물 1

HCID 674675792-(1-Benzylpiperidin-4-yloxy)-6-bromobenzo[d]thiazole수율 38.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Compound 1B (4.32 g, 13.79 mmol) in THF (100 mL) was added Et3N (3.84 mL, 27.6 mmol) followed by (bromomethyl)benzene (1.64 mL, 13.8 mmol). Upon completion of addition, the reaction mixture was stirred at rt overnight. After this time, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL), and then extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (40 mL) and dried (MgSO4). The solvent was removed and the resulting residue was recrystallized from MeOH to give Compound 14A as a white solid (2.12 g, 5.26 mmol, 38% yield). LC/MS (m/z)=404 (M+H)+.

후처리

  1. additionUpon completion of addition
  2. customAfter this time, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with brine (40 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed
  7. customthe resulting residue was recrystallized from MeOH

출처 및 근거

ORD 기록
ord-1a17b8ca462042afbe3bd11e77d235fe
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940716B2

반응 노트

불러오는 중…