Sodium Carbonate → HCID 68776419, compound

HRID 2261202Notes

Reaction equation

HRID 2261202 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9](=[O:18])[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])[CH:5]=[CH:6][CH:7]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>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.CN(C=O)C>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1[C:2]1[CH:3]=[C:4]([N:8]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9](=[O:18])[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 68774932HCID 68774932, compound

Product 1

HCID 68776419HCID 68776419, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Tert-butyl 2-(N-(3-bromophenyl)-2,6-difluorobenzamido)acetate (0.55 mmol) is mixed with 2,6-dimethoxyphenyl boronic acid (6.13 mmol) and Pd(Ph3P)4 (0.024 mmol). To the solid mixture under nitrogen, Na2CO3 2M (0.83 mL) is added followed by DMF (5.6 mL). The reaction mixture is stirred at room temperature for 1 hour and then heated at 85° C. for 12 hours. The reaction mixture is purified by automated column chromatography (gradient of hexanes and ethyl acetate) to give tert-butyl 2-(N-(3-(2,6-dimethoxyphenyl)phenyl)-2,6-difluorobenzamido)acetate: 1H NMR (400 MHz, CDCl3) δ7.19 (m, 6H), 6.69 (t, J=7.2 Hz, 2H), 6.58 (d. J=8.4 Hz, 2H), 4.46 (s, 2H), 3.64 (s, 6H), 1.48 (s, 9H); MS: (ES+) 484.1 (M+23)+.

Workup

  1. temperatureheated at 85° C. for 12 hours
  2. customThe reaction mixture is purified by automated column chromatography (gradient of hexanes and ethyl acetate)

Sources & evidence

ORD record
ord-09ed22c1ea9a4280a409e21e77781630
Source dataset
uspto-grants-2010_12
Patent number
US07846949B2

Reaction notes

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