Benzo(B)Thiophene-2-Boronic Acid → HCID 57562430, compound

HRID 1726095Notes

Reaction equation

HRID 1726095 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][P:18]([O:26][CH3:27])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])=[CH:14][CH:15]=2)[C:10](I)=[N:9]1)=O)(C)(C)C.[S:29]1[C:33](B(O)O)=[CH:32][C:31]2[CH:37]=[CH:38][CH:39]=[CH:40][C:30]1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:27][O:26][P:18]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)(=[O:19])[O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][N:9]=[C:10]2[C:33]1[S:29][C:30]2[CH:40]=[CH:39][CH:38]=[CH:37][C:31]=2[CH:32]=1

Participants

6

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10796Cesium carbonateHCID 86598868HCID 86598868, compound

Product 1

HCID 57562430HCID 57562430, compoundYield 2.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared according to procedure L employing 30 mg of 3-iodo-5-(methoxyphenylphosphinoyloxy)indazole-1-carboxylic acid tert-butyl ester, 21.2 mg of benzo[b]thiophene-2-boronic acid, 2.23 mg of 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride and 71 mg of cesium carbonate in 500 μl of dimethylformamide. 0.7 mg of phenylphosphonic acid 3-benzo[b]thiophen-2-yl-1H-indazol-5-yl ester methyl ester is isolated.

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-8165cfd438f54af1a08f37cbbc6125a9
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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