Water → HCID 178433039, compound

HRID 1695801Notes

Reaction equation

HRID 1695801 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]=[C:38]([NH:43][S:44]([CH:47]2[CH2:49][CH2:48]2)(=[O:46])=[O:45])[C:39]([OH:42])=[N:40][CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.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]>[CH:47]1([S:44]([NH:43][C:38]2[CH:37]=[C:36]([C:17]3[CH:16]=[C:15]4[C:11]([CH:12]=[N:13][NH:14]4)=[C:10]([NH:9][C:7]([C:5]4[N:6]=[C:2]([CH3:1])[S:3][CH:4]=4)=[O:8])[CH:18]=3)[CH:41]=[N:40][C:39]=2[OH:42])(=[O:45])=[O:46])[CH2:49][CH2:48]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 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 178527451HCID 178527451, compound

Product 1

HCID 178433039HCID 178433039, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent2×

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 (27.5 mg) was dissolved in 1,4-dioxane (0.5 ml) and N-(5-bromo-2-hydroxy-3-pyridinyl)cyclopropanesulfonamide (40 mg) was added. Sodium carbonate (48 mg) and Pd(dppf)Cl2 (8.3 mg) were weighed before further 1,4-dioxane (0.5 ml) and water (1 ml) were added. The reaction was heated under microwave irradiation at 140° C. for 20 min. The reaction was added to a silica SPE cartridge that was eluted with MeOH. The MeOH was evaporated to dryness and the residue was dissolved in DMSO:MeOH (1.6 ml, 1:1, v/v) and purified by MDAP (method F) to give the title compound (11 mg).

Workup

  1. additionwere added
  2. additionThe reaction was added to a silica SPE cartridge that
  3. washwas eluted with MeOH
  4. customThe MeOH was evaporated to dryness
  5. dissolutionthe residue was dissolved in DMSO
  6. customMeOH (1.6 ml, 1:1, v/v) and purified by MDAP (method F)

Sources & evidence

ORD record
ord-d8f01f85edaa47559cea1dc8d0db4cb2
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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