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

HRID 1429533ノート

反応式

HRID 1429533 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-1a17b8ca462042afbe3bd11e77d235fe
出典データセット
uspto-grants-2015_01
特許番号
US08940716B2

反応ノート

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