Sodium hydride → HCID 67482349, compound

HRID 1818636Notes

Reaction equation

HRID 1818636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[H-].[Na+].[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[CH:5]=[C:6]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:28][CH:29]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 67482349HCID 67482349, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-chloroindole-2-carboxylate (4.50 g, 20.1 mmol) in DMF (50 mL) was added NaH (885 mg, 60% suspension in mineral oil, 22.1 mmol). After 20 min, 4-tert-butylbenzyl bromide (4.07 mL, 22.1 mmol) was added. After 3 h, the reaction mixture was quenched by addition of sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc, and the organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20%, then 20 to 100% EtOAc in hexanes) provided the title compound: LCMS B, tr=3.18 min, m/z 370.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.71 (d, J=2.0 Hz, 1H), 7.35 (s, 1H), 7.33-7.27 (m, 4H), 7.01 (d, J=8.0 Hz, 2H), 5.84 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H), 1.30 (s, 9H).

Workup

  1. waitAfter 3 h
  2. customthe reaction mixture was quenched by addition of sat. aq. NH4Cl
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialthe organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 20%

Sources & evidence

ORD record
ord-1d89a9277d7a40d58996ff6b9f4adeb2
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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