Sodium Carbonate → HCID 86669235, compound

HRID 2366853Notes

Reaction equation

HRID 2366853 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][CH:16]=[O:17])[CH2:6][C@@H:5]1[CH3:18])(=[O:3])[CH3:2].[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].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:24]3[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:15][CH:16]=[O:17])[CH2:6][C@@H:5]1[CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86669233HCID 86669233, compound

Product 1

HCID 86669235HCID 86669235, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of [(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (for a preparation see Intermediate 43) (82 g, 0.263 mol) in DME (2 L) are added (4-formylphenyl)boronic acid (51.4 g, 0.34 mol) at room temperature. A 2N solution of Na2CO3 (527 mL, 1.05 mol) and tetrakis(triphenylphosphine)palladium(0) (8.2 g, 10% w/w) are added and the mixture is heated to reflux under a nitrogen atmosphere. After 2 hours, the reaction is complete and the mixture is concentrated under reduced pressure. The residue is taken up in water (1 L) and the darkened mixture is diluted with EtOAC (1 L) and transferred to a separatory funnel. A dark precipitate has formed and is isolated by filtration after separation of the organic phase. The organic layer is dried over Na2SO4 and delivers the title compound (37.5 g) as a yellow solid after concentration under reduced pressure and precipitation of the organic residue in a DCM/hexane mixture. The dark solid is taken up in a DCM/MeOH mixture and purified by flash chromatography on silica gel eluting with a 80/2 ratio of DCM/MeOH to afford the title compound (45 g) as a yellow brown solid. Mp: 85.6° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additionthe darkened mixture is diluted with EtOAC (1 L)
  5. customtransferred to a separatory funnel
  6. customA dark precipitate has formed
  7. customis isolated by filtration
  8. customafter separation of the organic phase
  9. dry with materialThe organic layer is dried over Na2SO4
  10. concentrationafter concentration
  11. customunder reduced pressure and precipitation of the organic residue in a DCM/hexane mixture
  12. custompurified by flash chromatography on silica gel eluting with a 80/2 ratio of DCM/MeOH

Sources & evidence

ORD record
ord-b0702bbff924436a9873646f768867d0
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…