1,4-Dioxane → HCID 71680470, compound

HRID 1777729Notes

Reaction equation

HRID 1777729 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12](Br)[S:13][C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[CH2:22][N:23]2[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[CH:25]=[CH:24]2)[CH2:17][CH2:16]1.O1CCO[CH2:36][CH2:35]1>>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]([CH2:35][CH3:36])[S:13][C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[CH2:22][N:23]2[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[CH:25]=[CH:24]2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 71680471HCID 71680471, compound

Product 1

HCID 71680470HCID 71680470, compound

Conditions

Temperature
100 °C

Procedure

A vial was charged with Example 38 (50 mg), 1,1′-bis(diphenylphosphin)ferrocen dichloropalladium-(II)-chlorid complex (in DCM 1/1, 3.91 mg) and dioxane (1.5 mL) at RT under argon, sealed and evacuated and backfilled with argon three times. Diethylzinc (1.5M in toluene) was added. The resulting orange suspension was shaken at 100° C. for 1.5 h. The reaction mixture was allowed to cool down, was quenched with water (0.5 mL) dropwise and evaporated to dryness. The resulting brown solid was purified by preparative LC-MS (I) to afford 17 mg of beige solid. LC-MS (A): tR=0.65 min; [M+H]+: 472.3.

Workup

  1. customsealed
  2. customevacuated
  3. additionDiethylzinc (1.5M in toluene) was added
  4. temperatureto cool down
  5. customwas quenched with water (0.5 mL) dropwise
  6. customevaporated to dryness
  7. customThe resulting brown solid was purified by preparative LC-MS (I)

Sources & evidence

ORD record
ord-7ebdfac0cdc74d75abc5da5827751916
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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