Water → HCID 58356402, compound

HRID 244761Notes

Reaction equation

HRID 244761 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([NH:12][C:13]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH2:26][C@H:25]([CH3:27])[O:24][C@H:23]([CH3:28])[CH2:22]3)[S:18][CH:19]=2)=[O:14])[CH:3]=1.[NH:29]1[C:37]2[C:32](=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>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].O1CCOCC1>[CH3:28][C@H:23]1[O:24][C@@H:25]([CH3:27])[CH2:26][N:21]([CH2:20][C:17]2[S:18][CH:19]=[C:15]([C:13]([NH:12][C:4]3[CH:3]=[C:2]([C:33]4[CH:34]=[CH:35][CH:36]=[C:37]5[C:32]=4[CH:31]=[CH:30][NH:29]5)[CH:10]=[C:9]4[C:5]=3[CH:6]=[N:7][N:8]4[CH3:11])=[O:14])[N:16]=2)[CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27631731H-Indole-4-boronic acidHCID 58255792HCID 58255792, compound

Product 1

HCID 58356402HCID 58356402, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

N-(6-Bromo-1-methyl-1H-indazol-4-yl)-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide (100 mg, 0.215 mmol), 1H-indol-4-ylboronic acid (38.1 mg, 0.237 mmol), Pd(dppf)Cl2 (15.76 mg, 0.022 mmol) and tripotassium phosphate (137 mg, 0.646 mmol) were placed into a microwave vial with water (0.300 mL) and 1,4-dioxane (1.5 mL) and the mixture heated at 100° C. in a microwave for 10 mins. The solvent was blown off and the residue partitioned between water (10 ml) and DCM (10 ml). The organic layer was collected using a hydrophobic frit and the solvent blown off. The residue was purified by chromatography on silica eluting with 0-100% ethyl acetate in cyclohexane followed by 0-25% methanol to give the title compound.

Workup

  1. customthe residue partitioned between water (10 ml) and DCM (10 ml)
  2. customThe organic layer was collected
  3. customThe residue was purified by chromatography on silica eluting with 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-525c0e6e53e14cbb9d2ae2710e7c7698
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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