Nitrogen → HCID 86696274, compound

HRID 2175151Notes

Reaction equation

HRID 2175151 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[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1.N#N.C([Sn](CCCC)(CCCC)[C:35]([O:37][CH2:38][CH3:39])=[CH2:36])CCC>O1CCOCC1.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>[CH2:38]([O:37][C:35]([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[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1)=[CH2:36])[CH3:39]

Participants

6

Reactant 3

HCID 947NitrogenHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86696275HCID 86696275, compound

Product 1

HCID 86696274HCID 86696274, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

The solution of (77.1) (110 mg, 0.249 mmol) and PdCl2(PPh3)2 (17.45 mg, 0.025 mmol) in 1,4-dioxane (4 ml) was bubbled by N2 for 5 min. Tributyl(1-ethoxyvinyl)stannane (135 mg, 0.373 mmol) was added. The reaction tube was flushed by N2 for 5 min again and sealed. The sealed-tube was stirred at 120° C. for 2 h. The reaction was evaporated to dryness and the residue was directly used in the next step. LCMS (method A): [M+H]+=433.6, tR=2.54 min.

Workup

  1. customThe reaction tube was flushed by N2 for 5 min again
  2. customsealed
  3. customThe reaction was evaporated to dryness

Sources & evidence

ORD record
ord-00208f1eec2c47d195bc1b8a17e1cf98
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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