1,4-Dioxane → HCID 86696270, compound

HRID 2175148Notes

Reaction equation

HRID 2175148 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][CH:25]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:24][CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1.[Sn].[O:37]1[CH2:42][CH2:41]O[CH2:39][CH2:38]1>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>[Si:29]([O:28][CH:25]1[CH2:26][CH2:27][N:22]([C:16]2[CH:17]=[N:18][C:19]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:11][C:8]2[N:6]4[CH:7]=[C:2]([C:38]([O:37][CH2:42][CH3:41])=[CH2:39])[CH:3]=[CH:4][C:5]4=[N:10][N:9]=2)=[CH:21][CH:20]=3)[CH2:23][CH2:24]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 5352426Tin atomHCID 86696271HCID 86696271, compound

Product 1

HCID 86696270HCID 86696270, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

The solution of (76.1) (100 mg, 0.175 mmol) and PdCl2(PPh3)2 (12.30 mg, 0.018 mmol) in 1,4-Dioxane (2 ml) was bubbled with Argon for 5 mins, Tin reagent (95 mg, 0.263 mmol) was added by injection and the mixture was bubbled with Argon for another 5 mins, and the tube was sealed and heated to 120° C. for 3 hr. Monitored the reaction by TLC. The solvent was evaporated and the residue was purified by flash chromatography and eluented with DCM/MeOH (40:1˜20:1) to give pure desired product (76.2) as orange oil (90 mg, yield 90%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.73 (s, 1H), 8.41 (s, 1H), 7.97 (d, 1H), 7.78 (d, 1H), 7.57 (s, 2H), 7.42-7.49 (m, 2H), 7.21 (s, 1H), 4.68 (s, 1H), 4.36 (s, 1H), 3.88-3.98 (m, 3H), 3.48-3.53 (m, 2H), 3.18-3.23 (m, 2H), 1.88-1.91 (m, 2H), 1.66-1.74 (m, 2H), 1.38 (t, 3H), 0.91 (s, 9H), 0.09 (s, 6H).

Workup

  1. customthe mixture was bubbled with Argon for another 5 mins
  2. customthe tube was sealed
  3. customMonitored the reaction by TLC
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-245834338d0b4df8918f31ddaf8e9c4b
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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