2-Thiopheneboronic acid → HCID 69354355, compound

HRID 1182241Notes

Reaction equation

HRID 1182241 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([NH:14][C:15]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:13].[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O>C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.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>[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([NH:14][C:15]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:13]

Participants

6

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 10271514HCID 10271514, compound

Product 1

HCID 69354355HCID 69354355, compoundYield 4.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-{[(5-bromo-1H-indol-3-yl)acetyl]amino}-4-methylbenzoic acid (product of example 6, 48 mg), thiophene-2-boronic acid (17 mg), tetrakis(triphenylphosphine)palladium(0) (12 mg) was heated in a mixture of 2M sodium carbonate solution (0.5 ml) and dimethoxyethane (0.5 ml) for 18 h at 80° C. The mixture was concentrated and diluted with DCM, then washed with 2N HCl for 1 hr. The solvent was reduced and the residue purified by mass-directed automated HPLC to give the title compound (2 mg). MH+391.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with DCM
  3. washwashed with 2N HCl for 1 hr
  4. customthe residue purified

Sources & evidence

ORD record
ord-32d4233909ae4e6f85406762b6125c63
Source dataset
uspto-grants-2007_10
Patent number
US07288564B2

Reaction notes

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