Tri(butyl)vinyltin → 7-methoxy-2-phenyl-6-vinylquinolin-4(1H)-one

HRID 1360105Notes

Reaction equation

HRID 1360105 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:6][C:5]2=[O:20].[CH2:21](C([Sn])=C(CCCC)CCCC)[CH2:22]CC>CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:20])[CH:6]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:8]2)=[CH:3][C:2]=1[CH:21]=[CH2:22]

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 57617105HCID 57617105, compound

Product 1

HCID 576171267-methoxy-2-phenyl-6-vinylquinolin-4(1H)-oneYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one (1.0 g, 3.03 mmol) in DMSO (35 mL) was added tri(n-butyl)vinyltin (1.06 mL, 3.63 mmol) and finally tetrakis(triphenylphosphine)palladium (88 mg, 0.076 mmol). The mixture was then degassed using a freeze/pump/thaw cycle (2×). The mixture was then heated to 100° C. in a sealed tube for 22 h. At this time, LC-MS revealed complete consumption of the bromoquinoline). The reaction mixture was then poured into a mixture of water (200 mL) and EtOAc (200 mL) which caused solid to crash out. The solid was filtered off, washed with CH3CN, EtOAc, DCM, and then hexanes to give 7-methoxy-2-phenyl-6-vinylquinolin-4(1H)-one as a light greenish solid (670 mg, 80%). 1H NMR (400 MHz, DMSO-d6) ppm: 11.58 (s, 1H), 8.16 (s, 1H), 7.83 (m, 2H), 7.58 (m, 3H), 7.25 (s, 1H), 6.99 (dd, J=11 Hz, 17.5 Hz, 1H), 6.28 (s, 1H), 5.85 (d, J=17.5 Hz, 1H), 5.31 (d, J=11 Hz, 1H), 3.92 (s, 3H). LRMS (CI, [M+H]) Calc'd=278.1. found=278.2.

Workup

  1. customThe mixture was then degassed
  2. customconsumption of the bromoquinoline)
  3. additionThe reaction mixture was then poured into a mixture of water (200 mL) and EtOAc (200 mL) which
  4. filtrationThe solid was filtered off
  5. washwashed with CH3CN, EtOAc, DCM

Sources & evidence

ORD record
ord-55d57672ceac41509d0723169341317a
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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