N-bromobutanimide → HCID 53837501, compound

HRID 1811034Notes

Reaction equation

HRID 1811034 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][N:14]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C1COCC1.CCOCC>[Br:24][C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 54064886HCID 54064886, compound

Product 1

HCID 53837501HCID 53837501, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step 3 A solution of tert-butyl 6-(4-fluorophenyl)-1H-indole-1-carboxylate (187.8 mg, 0.603 mmol) in THF (4 mL) was treated with N-bromosuccinimide (118 mg, 0.663 mmol) and stirred at rt. After 18 h, the solution was diluted with ether, washed with 2×10 mL aqueous sodium bisulfite (ca. 1.5 M), then with NaHCO3 (aq), dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 90:10 hexane-EtOAc) provide tert-butyl 3-bromo-6-(4-fluorophenyl)-1H-indole-1-carboxylate as a white glassy foam (134 mg, 57%). 1H NMR (400 MHz, chloroform-d) δ 8.39 (1 H, br. s.), 7.59-7.68 (3 H, m), 7.54-7.59 (1 H, m), 7.48-7.53 (1 H, m), 7.14 (2 H, t, J=8.7 Hz), 1.67 (9 H, s).

Workup

  1. washwashed with 2×10 mL aqueous sodium bisulfite (ca. 1.5 M)
  2. dry with materialwith NaHCO3 (aq), dried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (
  5. washeluting with a gradient from hexane to 90:10 hexane-EtOAc)

Sources & evidence

ORD record
ord-6c8b107b54e44efb8fa07998107c2331
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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