Potassium Carbonate → HCID 22390167, compound

HRID 1072340Notes

Reaction equation

HRID 1072340 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:17])[C:9]2[N:10]=[CH:11][N:12]3[CH:16]=[CH:15][S:14][C:13]=23)[CH:5]=[N:6][CH:7]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>[O-2].[O-2].[Mn+4].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]1([C:2]2[CH:3]=[C:4]([C:8]([C:9]3[N:10]=[CH:11][N:12]4[CH:16]=[CH:15][S:14][C:13]=34)=[O:17])[CH:5]=[N:6][CH:7]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 22390351HCID 22390351, compound

Product 1

HCID 22390167HCID 22390167, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 178418406HCID 178418406, compoundCatalyst

Procedure

A ketone compound (1.96 g) was prepared in substantially the same manner as in step b) of Synthesis Example 1, except that 2.77 g of 7-[(5-bromopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole and 2.00 g of manganese dioxide were used as the starting compounds. 7-(5-Phenylpyridin-3-yl)carbonylimidazo[5,1-b]thiazole (285 mg) was prepared in substantially the same manner as in step b) of Synthesis Example 11, except that 308 mg of the ketone compound, 240 mg of phenylboronic acid, 116 mg of tetrakis(triphenylphosphine)palladium(0), and 276 mg of potassium carbonate were used as the starting compounds.

Workup

  1. customof Synthesis Example 1
  2. customof Synthesis Example 11

Sources & evidence

ORD record
ord-5480d79b56fc4e29a8ddb6c49d63b808
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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