Sodium Carbonate → HCID 18457809, compound

HRID 1272701Notes

Reaction equation

HRID 1272701 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[O:7])=[CH:4][CH:3]=1.B.[C:16]([C:19]1[CH:20]=[C:21](CC(C(O)(C)C)(C)O)[C:22]([CH3:25])=[CH:23][CH:24]=1)([OH:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH:10]1([CH2:9][NH:8][C:6]([C:5]2[CH:13]=[CH:14][C:2]([C:23]3[C:22]([CH3:25])=[CH:21][CH:20]=[C:19]([C:16]([OH:18])=[O:17])[CH:24]=3)=[CH:3][CH:4]=2)=[O:7])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 184578074-Bromo-N-(cyclopropylmethyl)benzamideHCID 178419166HCID 178419166, compound

Product 1

HCID 18457809HCID 18457809, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromo-N-cyclopropylmethylbenzamide (2.0 g, 7.87 mmol), (3-carboxy-6-methylphenyl) pinacol borane (2.06 g, 7.87 mmol), tetrakis(triphenylphosphine)palladium (900 mg, 0.79 mmol) and aqueous sodium carbonate (1M, 50 ml) in DME (100 ml) were heated at 90° C. for 18 h. The organic phase was absorbed onto silica and purified by flash chromatography (silica) eluting with DCM/ethanol/ammonia (20:8:1) to give {4′-[(cyclopropylmethylamino)carbonyl]-6-methyl-1,1′-biphenyl-3-yl}carboxylic acid (1.9 g, 78%). LCMS: retention time 3.18 min, MH+310.

Workup

  1. customThe organic phase was absorbed onto silica
  2. custompurified by flash chromatography (silica)
  3. washeluting with DCM/ethanol/ammonia (20:8:1)

Sources & evidence

ORD record
ord-bc02c4b53a41417f85c01724a337ea5a
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

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