Oxalyl chloride → HCID 59298800, compound

HRID 63574Notes

Reaction equation

HRID 63574 reaction equation
C1([C@H]2[C@H](C3C4C(=CC=CC=4)NC=3)C(=O)NC2=O)C2=C3C(=CC=C2)CCCN3C=1.[CH2:29]([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][C:39]=2[Br:41])[CH:34]=[CH:33]1)[CH:30]=[CH2:31].[C:42](Cl)([C:44](Cl)=[O:45])=[O:43].[CH3:48][O-:49].[Na+]>ClCCl>[CH3:48][O:49][C:44](=[O:45])[C:42]([C:34]1[C:35]2[C:40](=[C:39]([Br:41])[CH:38]=[CH:37][CH:36]=2)[N:32]([CH2:29][CH:30]=[CH2:31])[CH:33]=1)=[O:43]

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 10942334Sodium MethoxideHCID 110643941-allyl-7-bromo-1H-indoleHCID 11494412Tivantinib

Product 1

HCID 59298800HCID 59298800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-yl)-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-yl)-4-(1H-indol-3-yl)-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-be29c61897724e6f88b6f0637ce31be9
Source dataset
uspto-grants-2016_09
Patent number
US09447088B2

Reaction notes

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