Phosphorus tribromide → HCID 22155939, compound

HRID 475287Notes

Reaction equation

HRID 475287 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH:20](O)[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].P(Br)(Br)[Br:24].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOCC>[Br:24][CH:20]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH:13]=[CH:12][N:11]2[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])[CH3:21]

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 13799992HCID 13799992, compound

Product 1

HCID 22155939HCID 22155939, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 282 (400 mg, 1.27 mmol) in dry DCM (2 mL) and dry Et2O (2 mL) at 0° C. under Argon was added PBr3 (515 mg, 1.91 mmol) and the mixture was stirred at RT overnight. The mixture was poured into cold NaHCO3 (aq.) and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 450 mg (92%) of 4-(1-bromoethyl)-1-tosyl-1H-indole (284) give as a yellow oil, which was used in the next step without further purification: 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 2H), 7.65 (d, J=2.8 Hz, 1H), 7.35-7.23 (m, 4H), 6.89 (d, J=2.8 Hz, 1H), 5.53-5.50 (m, 1H), 2.36 (s, 3H), 2.13 (d, J=6.8 Hz, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed sequentially with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2b453ef8b33466c97d4c702d94986d6
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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