L-Proline → 6-[1,1';3',1'']-Terphenyl-5'-yl-6H-benzo[c][2,6]naphthyridin-5-one

HRID 523445Notes

Reaction equation

HRID 523445 reaction equation
[C:1]1(=O)[NH:10][CH:9]=[CH:8][C:7]2[CH:6]=[N:5][C:4]3[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=3[C:2]1=2.I[C:17]1[CH:18]=[C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:22]=1.N1CCC[C@H]1C(O)=[O:38]>O>[C:29]1([C:19]2[CH:18]=[C:17]([N:5]3[C:4]4[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=4[C:2]4[C:7](=[CH:8][CH:9]=[N:10][CH:1]=4)[C:6]3=[O:38])[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 10241772Benzo[c]-2,6-napthyridinoneHCID 130672305'-Iodo-m-terphenyl

Product 1

HCID 867326596-[1,1';3',1'']-Terphenyl-5'-yl-6H-benzo[c][2,6]naphthyridin-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.6 g (100 mmol) of benzo[c]-2,6-napthyridinone, 106 g (300 mmol) of 5′-iodo-[1,1′;3′,1″]terphenyl and 2.3 g (20 mmol) of L-proline are stirred at 150° C. in 100 ml for 30 h The solution is diluted with water, extracted twice with ethyl acetate, the combined organic phases are dried over Na2SO4 and evaporated in a rotary evaporator. The residue is purified by chromatography (EtOAc/hexane: 2/3). The yield is 25 g (59 mmol) 60% of theory.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe combined organic phases are dried over Na2SO4
  3. customevaporated in a rotary evaporator
  4. customThe residue is purified by chromatography (EtOAc/hexane: 2/3)

Sources & evidence

ORD record
ord-c749483b1c3141d3a2fba2640dccae58
Source dataset
uspto-grants-2016_05
Patent number
US09337430B2

Reaction notes

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