Benzyl Bromide → HCID 21084555、化合物

HRID 347937ノート

反応式

HRID 347937 の反応式
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.CC([O-])(C)C.[K+].[C:17]1([CH2:23]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:23]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([I:1])=[CH:3]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 112072533-iodo-1H-indoleHCID 23665647Potassium tert-butoxide

生成物 1

HCID 21084555HCID 21084555、化合物収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-iodoindole (1, 2.9 g, 11.93 mmol) in THF (50 mL) is added t-BuOK (1.6 g, 14.26 mmol) at 0° C. After 1 h, PhCH2Br (3.0 g, 17.54 mmol) is added dropwise over 20 min at 0° C. The reaction is then warmed to room temperature and stirred for additional 4 h, then concentrated under reduced pressure. The residue is partitioned between EtOAc (60 mL) and H2O (30 mL). The organic layer is dried (MgSO4). The solvent is then removed and purification by flash column chromatography from EtOAc-n-hexane to give 1.98 g (52%) of 2: 1H NMR (CDCl3): δ7.94–7.98 (m, 1H), 7.41–7.45 (m, 2H), 7.13–7.35 (m, 5H), 6.47–6.54 (m, 2H), 5.33 (s, 2H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is partitioned between EtOAc (60 mL) and H2O (30 mL)
  3. dry with materialThe organic layer is dried (MgSO4)
  4. customThe solvent is then removed
  5. custompurification by flash column chromatography from EtOAc-n-hexane

出典と根拠

ORDレコード
ord-a244bcf74d884f00b1ebbcd7b6ff1329
出典データセット
uspto-grants-2007_02
特許番号
US07176230B2

反応ノート

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