Carbon tetrabromide → 3-(3-Bromopropyl)-5-nitro-1H-indole

HRID 441075Notes

Reaction equation

HRID 441075 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][CH2:33][CH2:34]O)([O-:22])=[O:21].C(Br)(Br)(Br)[Br:37]>C(#N)C>[Br:37][CH2:34][CH2:33][CH2:32][C:26]1[C:25]2[C:29](=[CH:30][CH:31]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[NH:28][CH:27]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 199620365-Nitro-3-(3-hydroxypropyl)-1H-indole

Product 1

HCID 199620433-(3-Bromopropyl)-5-nitro-1H-indoleYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a solution of triphenylphosphine (6.70 g, 0.025 mol) in 80 mL of acetonitrile was added a solution of 5-nitro-3-(3-hydroxypropyl)indole (18) (4.30 g, 0.020 mol) in 75 mL of acetonitrile, followed by a solution of CBr4 (9.00 g, 0.027 mol) in 25 mL of acetonitrile, at 0° C. under Ar. The mixture was stirred at room temperature for 3 h and then it was evaporated and the residue was chromatographed (SiO2 /ethyl acetate-hexane, 1:9 then 1:4) to give the title compound (4.60 g, 84%) as a solid, mp 92°-95° C.: IR (neat) 3420, 1330 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ 8.59 (d, J=2.1 Hz, 1H), 8.40 (br s, 1H), 8.13 (dd, J=9.0, 2.2 Hz, 1H), 7.40 (d, J=9.1 Hz, 1H), 7.21 (d, J=2.2 Hz, 1H), 3.45 (t, J=6.4 Hz, 2H), 2.99 (t, J=7.2 Hz, 2H), 2.26 (m, 2H).

Workup

  1. customit was evaporated
  2. customthe residue was chromatographed (SiO2 /ethyl acetate-hexane, 1:9

Sources & evidence

ORD record
ord-b5f966f182254819a80db1ce8da61b7d
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

Loading…