Potassium Phosphate, Tribasic → HCID 22032135, compound

HRID 1792593Notes

Reaction equation

HRID 1792593 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]([C:33]3[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=3)=[N:11][N:12]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:13]=2)O1.Br[C:44]1[CH:45]=[CH:46][C:47]2[N:48]([C:50]([C:53]3[S:54][CH:55]=[CH:56][N:57]=3)=[CH:51][N:52]=2)[CH:49]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[S:54]1[CH:55]=[CH:56][N:57]=[C:53]1[C:50]1[N:48]2[CH:49]=[C:44]([C:9]3[C:10]([C:33]4[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=4)=[N:11][N:12]([C:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[CH:45]=[CH:46][C:47]2=[N:52][CH:51]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 22031126HCID 22031126, compoundHCID 22032257HCID 22032257, compound

Product 1

HCID 22032135HCID 22032135, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g methyl 5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]-2-thiophene carboxylate (compound in Production Example 117), 0.6 g 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)-1,3-thiazole (compound in Production Example 57), 0.68 g tripotassium phosphate, 0.12 g tetrakis (triphenylphosphine)palladium and 30 mL N,N-dimethylformamide were heated at 85° C. for 2.5 hours under nitrogen atmosphere. After the solvent was removed, the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give 1.2 g of the title compound.

Workup

  1. customAfter the solvent was removed
  2. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c453be8c9efc4469a0508b0dcac3dd58
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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