HCID 59470966, compound → 1-allyl-7-bromo-1H-indole

HRID 388347Notes

Reaction equation

HRID 388347 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[Br:13])[C:6](C2C(=O)NC(=O)C=2C2C3C(=CC=CC=3)NC=2)=[CH:5]1)[CH:2]=[CH2:3]>CO>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[Br:13])[CH:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 59470966HCID 59470966, compound

Product 1

HCID 110643941-allyl-7-bromo-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-Trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1H-indol-3-yl)pyrrolidine-2,5-dione may be prepared by reacting 1-allyl-7-bromo-1H-indole with (COCl)2 (oxalyl chloride) and sodium methoxide in a polar aprotic solvent such as dichloromethane to yield (1-allyl-7-bromo-1H-indol-3-yl)-oxo-acetic acid methyl ester, which is subsequently reacted with 2-(1H-indol-3-yl)-acetamide and tBuOK (potassium tert-butoxide) in THF to yield 3-(1-allyl-7-bromo-1H-indol-3-O-4-(1H-indol-3-yl)-pyrrole-2,5-dione. Reduction of the 3-(1-allyl-7-bromo-1H-indol-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione by Mg in refluxing methanol, as in Example 2 procedure C, yields 3-(1-allyl-7-bromo-1H-indol-3-O-4-(1H-indol-3-O-pyrrolidine-2,5-dione, which is treated with 9-BBN (9-borabicyclo[3.3.1]nonane) and Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium) to yield (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1H-indol-3-yl)pyrrolidine-2,5-dione.

Sources & evidence

ORD record
ord-c5d8d0eedb1047cdad852a66dc84359b
Source dataset
uspto-grants-2013_02
Patent number
US08377927B2

Reaction notes

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