Sodium Carbonate → HCID 44539625, compound

HRID 1695805Notes

Reaction equation

HRID 1695805 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[C:11]3[C:15]([CH:16]=[C:17](B4OC(C)(C)CC(C)(C)O4)[CH:18]=2)=[N:14][N:13](C2CCCCO2)[CH:12]=3)=[O:8])[N:6]=1.Br[C:36]1[CH:37]=[CH:38][C:39]([Cl:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>CO.Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:47][C:39]1[CH:38]=[CH:37][C:36]([C:17]2[CH:16]=[C:15]3[C:11]([CH:12]=[N:13][NH:14]3)=[C:10]([NH:9][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[S:3][CH:4]=3)=[O:8])[CH:18]=2)=[CH:41][C:40]=1[NH:42][S:43]([CH3:46])(=[O:45])=[O:44]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 582558332-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamideHCID 62909797HCID 62909797, compound

Product 1

HCID 44539625HCID 44539625, compoundYield 36.1%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (55 mg), N-(5-bromo-2-chlorophenyl)methanesulfonamide (39 mg), sodium carbonate (48 mg) and Pd(dppf)Cl2 (8.3 mg) were weighed to a microwave vial. 1,4-Dioxane (0.5 ml) and water (0.5 ml) were added and the reaction was heated under microwave irradiation at 140° C. for 20 min. The reaction was passed through a 1 g silica SPE cartridge preconditioned with MeOH, washing with MeOH, the evaporated to dryness. The residue was dissolved in DMSO:MeOH (1:1, v/v, 1 ml) and purified by MDAP (method E). The residue obtained was dissolved in MeOH and a couple of drops of 2M HCl (aq) were added. The reaction was stirred for 2 h and evaporated to dryness to give the title compound (19 mg).

Workup

  1. washwashing with MeOH
  2. customthe evaporated to dryness
  3. dissolutionThe residue was dissolved in DMSO:MeOH (1:1, v/v, 1 ml)
  4. custompurified by MDAP (method E)
  5. customThe residue obtained
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-2c402367a3084649977965b6b59fa192
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

Loading…