Sodium Carbonate → HCID 90412392, compound

HRID 1850697Notes

Reaction equation

HRID 1850697 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[C:12]([CH3:17])=[N:13][S:14][C:15]=1[NH2:16].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:17][C:12]1[C:11]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[C:15]([NH2:16])[S:14][N:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 177499314-Bromo-3-methyl-1,2-thiazol-5-amine

Product 1

HCID 90412392HCID 90412392, compound

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

3-pyridylboronic acid (127.3 mg, 1.036 mmol), 4-bromo-3-methyl-isothiazol-5-amine (100 mg, 0.518 mmol), Na2CO3 (777 μL of 2 M, 1.554 mmol), palladium triphenylphosphane (29.93 mg, 0.0259 mmol) in dioxane (6 mL) was heated at 110° C. in a microwave for 30 min. The mixture was concentrated in vacuo and the residue was loaded on a SCX column, washed with DCM/MeOH mixtures before the product was eluted with a 2M solution of ammonia in MeOH. The eluent was concentrated in vacuo to yield 3-methyl-4-(pyridin-3-yl)isothiazol-5-amine as a pale yellow oil that was used in next step without further purification. MS (ES+) 192.0.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with DCM/MeOH mixtures before the product
  3. washwas eluted with a 2M solution of ammonia in MeOH
  4. concentrationThe eluent was concentrated in vacuo

Sources & evidence

ORD record
ord-ab29717418f64c319e2b921eef2c45cc
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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