methyl 7-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxy-carbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate → Methyl 7-[N-{2-((Z)-3-Diethylaminoprop-1-enyl)-4-fluoro-benzenesulfonyl}-N-(methoxycarbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927912Notes

Reaction equation

HRID 927912 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\C1C=C(F)C=CC=1S(NC1C(C(OC)=O)=C2C(C3C=COC=3CO2)=CC=1)(=O)=O)[CH3:2].Br[C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=1[S:45]([N:48]([C:53]1[C:62]([C:63]([O:65][CH3:66])=[O:64])=[C:61]2[C:56]([C:57]3[CH2:69][CH2:68][O:67][C:58]=3[CH:59]=[N:60]2)=[CH:55][CH:54]=1)[C:49]([O:51][CH3:52])=[O:50])(=[O:47])=[O:46].C(N(CC)C/C=C\[Sn](CCCC)(CCCC)CCCC)C>>[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\[C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=1[S:45]([N:48]([C:53]1[C:62]([C:63]([O:65][CH3:66])=[O:64])=[C:61]2[C:56]([C:57]3[CH2:69][CH2:68][O:67][C:58]=3[CH:59]=[N:60]2)=[CH:55][CH:54]=1)[C:49]([O:51][CH3:52])=[O:50])(=[O:47])=[O:46])[CH3:2]

Participants

4

Reactant 3

HCID 71006926methyl 7-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxy-carbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate2×HCID 86684725Methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylateHCID 86684726N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)amine2×

Product 1

HCID 86713282Methyl 7-[N-{2-((Z)-3-Diethylaminoprop-1-enyl)-4-fluoro-benzenesulfonyl}-N-(methoxycarbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate

Conditions

Temperature
60 °C

Procedure

Prepared by proceeding in a similar manner to Intermediate 9, starting from methyl 7-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxycarbonyl)amino]-1,2-dihydro-furo[2,3-c]quinoline-6-carboxylate (Intermediate 21) and N,N-diethyl-N—((Z)-1-tributylstannanylprop-1-en-3-yl)amine (Intermediate 11) and heating at 60° C. for 1 hour.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-26fad2181d40484ba2d4e3109b2ab721
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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