Benzyl Bromide → HCID 21084555, compound

HRID 347937Notes

Reaction equation

HRID 347937 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 21084555HCID 21084555, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a244bcf74d884f00b1ebbcd7b6ff1329
Source dataset
uspto-grants-2007_02
Patent number
US07176230B2

Reaction notes

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