Sodium Bicarbonate → HCID 86076887, compound

HRID 2377262Notes

Reaction equation

HRID 2377262 reaction equation
I[C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][C:9]([CH:14]=[O:15])=[CH:10][CH:11]=3)[C:4]=2[NH:5][N:6]=1.[S:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.C(=O)(O)[O-].[Na+]>COCCOC.O.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:16]1[CH:20]=[CH:19][C:18]([C:2]2[C:3]3[CH2:13][C:12]4[C:7](=[CH:8][C:9]([CH:14]=[O:15])=[CH:10][CH:11]=4)[C:4]=3[NH:5][N:6]=2)=[CH:17]1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 581760Thiophene-3-boronic acidHCID 178519294HCID 178519294, compound

Product 1

HCID 86076887HCID 86076887, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 319 (930 mg, 3.0 mmol), 3-thienylboronic acid (384 mg, 3.0 mmol), tetrakis(triphenylphosphine)palladium(0) (240 mg, 0.21 mmol) and sodium bicarbonate (630 mg, 7.5 mmol) in 1,2-dimethoxyethane (18 mL) and water (6 mL) was stirred under nitrogen in a heavy walled process vial in a microwave synthesizer at about 160° C. for about 10 minutes. The mixture was concentrated under vacuum and the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (3:1) as eluent to provide 240 mg (30%) of the desired product. MS (ESI): m/z 267 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e16377bd6ad3474aa0c00ad53318fdda
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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