Nitrogen → HCID 86696283, compound

HRID 2175155Notes

Reaction equation

HRID 2175155 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([N:22]3[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1.N#N.C([Sn](CCCC)(CCCC)[C:37]([O:39][CH2:40][CH3:41])=[CH2:38])CCC>CN(C=O)C.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>[CH2:40]([O:39][C:37]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([N:22]3[CH2:26][CH2:25][C@H:24]([N:27]([CH3:28])[CH3:29])[CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1)=[CH2:38])[CH3:41]

Participants

6

Reactant 3

HCID 947NitrogenHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86696284HCID 86696284, compound

Product 1

HCID 86696283HCID 86696283, compoundYield 13.91%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

The solution of (81.1) (256.5 mg, 0.546 mmol) and PdCl2(PPh3)2 (38.4 mg, 0.055 mmol) in DMF (10 ml) was bubbled by N2 for 5 min. Tributyl(1-ethoxyvinyl)stannane (296 mg, 0.820 mmol) was added. The reaction tube was flushed by N2 for 5 min again and sealed. The sealed-tube was stirred at 85° C. for 16 h. The mixture was evaporated to dryness and the residue was purified by flash chromatography (CombiFlash, ISCO, eluent MeOH/DCM from 0 to 10%) to afford the title compound (35 mg, yield 13.91%). LCMS (method A): [M+H]+=461.2, tR=1.96 min.

Workup

  1. customThe reaction tube was flushed by N2 for 5 min again
  2. customsealed
  3. customThe mixture was evaporated to dryness
  4. customthe residue was purified by flash chromatography (CombiFlash, ISCO, eluent MeOH/DCM from 0 to 10%)

Sources & evidence

ORD record
ord-1f4bcde500564e8eb935b66f3c8eb84f
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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