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

HRID 53145Notes

Reaction equation

HRID 53145 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=2)[NH:26][CH:25]=1.C(Br)(Br)(Br)[Br:37]>C(#N)C>[Br:37][CH2:21][CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=2)[NH:26][CH:25]=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 3-[3-hydroxypropyl]-5-nitro-1H-indole (Example 3) (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) δ8.59 (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-3dc77aea71c44d20ae1c668e1fc408e6
Source dataset
uspto-grants-1997_04
Patent number
US05618816

Reaction notes

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