Tri(butyl)vinylstannane → HCID 58016050, compound

HRID 1776154Notes

Reaction equation

HRID 1776154 reaction equation
I[C:2]1[S:3][C:4]2[NH:5][C:6](=[O:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[CH2:16](C([SnH3])=C(CCCC)CCCC)[CH2:17]CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH:16]([C:2]1[S:3][C:4]2[NH:5][C:6](=[O:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1)=[CH2:17]

Participants

5

Reactant 2

HCID 21115800Tri(butyl)vinylstannaneHCID 58016054HCID 58016054, compound

Product 1

HCID 58016050HCID 58016050, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

Bis(triphenylphosphine)palladium dichloride (0.005 g, 0.007 mmol) was added to a solution of 2-iodo-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one (0.115 g, 0.35 mmol) and DMF (5 ml) at 23° C. After 30 minutes, tributylvinylstannane (0.11 ml, 0.37 mmol) was added, and the reaction mixture was stirred overnight at 45° C. All volatiles were evaporated, and the resulting oil was purified by flash-chromatography (CH2Cl2/methanol, 99/1) to afford the title compound as a yellow solid (a quantitative yield). m.p 235-239° C. (dec.); 1H NMR (200 MHz, DMSO) δ 5.55 (d, 1H, CHH, J=11 Hz), 5.95 (d, 1H, CHH, J=17 Hz), 6.85-7.00 (m, 1H, CH), 7.47-7.54 (m, 1H, Ar), 7.74-7.82 (m, 1H, Ar), 8.09-8.20 (m, 2H, Ar), 12.43 (bs, 1H, NH).

Workup

  1. customAll volatiles were evaporated
  2. customthe resulting oil was purified by flash-chromatography (CH2Cl2/methanol, 99/1)

Sources & evidence

ORD record
ord-3d37c3e4727c47b1879098575586396a
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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