Sodium Carbonate → HCID 86669133, compound

HRID 2201321Notes

Reaction equation

HRID 2201321 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[CH:7]([NH:15][CH:16]=[O:17])[CH2:6][CH:5]1[CH3:18])(=[O:3])[CH3:2].[CH3:19][O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].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>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:26]3[CH:27]=[CH:28][C:23]([C:21]([O:20][CH3:19])=[O:22])=[CH:24][CH:25]=3)=[CH:11][CH:12]=2)[CH:7]([NH:15][CH:16]=[O:17])[CH2:6][CH:5]1[CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 86669134HCID 86669134, compound

Product 1

HCID 86669133HCID 86669133, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of intermediate 3 (1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)formamide (62.24 g) in DME (600 ml) was added palladium tetrakis (11.56 g) at room temperature. After 10 min of stirring, were added {4-[(methyloxy)carbonyl]phenyl}boronic acid (54 g) and a 2N solution of Na2CO3 (300 mL) and the mixture was stirred heated to reflux for 16 h. The mixture was concentrated under reduced pressure. After addition of 200 ml of DCM to the residue, the product precipitated, it was filtered and washed with water (3*100 mL). To remove the rest of the water, the solid was washed with isopropyl ether (100 ml), the solid was then added to 220 ml of warm isopropyl ether and the resulting mixture was left in the sonicator. The solid was filtered off and dried to afford the title compound as a beige solid (64.7 g)

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionAfter addition of 200 ml of DCM to the residue
  5. customthe product precipitated
  6. filtrationit was filtered
  7. washwashed with water (3*100 mL)
  8. customTo remove the rest of the water
  9. washthe solid was washed with isopropyl ether (100 ml)
  10. additionthe solid was then added to 220 ml of warm isopropyl ether
  11. waitthe resulting mixture was left in the sonicator
  12. filtrationThe solid was filtered off
  13. customdried

Sources & evidence

ORD record
ord-5c973101a413449b8dd4ddde59b5411e
Source dataset
uspto-grants-2016_06
Patent number
US09360482B2

Reaction notes

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