Dichloromethane → HCID 67111831, compound

HRID 1177511Notes

Reaction equation

HRID 1177511 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([C:13](B(O)O)=[CH2:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:18]1[CH2:23][CH2:22][CH2:21][O:20][CH:19]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:31][C:32]3[C:33]([N:39]=2)=[N:34][C:35](Cl)=[CH:36][CH:37]=3)=[C:26]([F:40])[CH:25]=1.C(Cl)Cl>O1CCOCC1.O>[O:20]1[CH2:21][CH2:22][CH2:23][O:18][CH:19]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:31][C:32]3[C:33]([N:39]=2)=[N:34][C:35]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH2:14])=[CH:36][CH:37]=3)=[C:26]([F:40])[CH:25]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 5003684(1-Phenylvinyl)boronic acidHCID 86638718HCID 86638718, compound

Product 1

HCID 67111831HCID 67111831, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A slurry of (amphos)2PdCl2 (0.0333 g, 0.0470 mmol), potassium carbonate (0.442 g, 3.20 mmol), 1-phenylvinylboronic acid (0.306 g, 2.07 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[4,5-b]pyridine (0.330 g, 0.941 mmol) in 4.5 mL dioxane and 1 mL water was flushed with argon and sealed, and heated to 80° C. overnight. The reaction mixture was cooled and treated with water and DCM. The aq. Layer was extracted with DCM, and the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was suspended in 2 mL MTBE and filtered, rinsing with 1 mL MTBE, to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[4,5-b]pyridine as a gray solid. MS (ESI) m/z: calculated: 418.1; Observed: 419.0 (M++1).

Workup

  1. customsealed
  2. temperatureThe reaction mixture was cooled
  3. extractionThe aq. Layer was extracted with DCM
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. washrinsing with 1 mL MTBE

Sources & evidence

ORD record
ord-53e75d038e044b1c95cc10617247d93d
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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