Sodium Bicarbonate → HCID 68406982, compound

HRID 888020Notes

Reaction equation

HRID 888020 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][C:33]=2B(O)O)[CH:28]=[CH:27][CH:26]=1.C(=O)([O-])O.[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.COCCOC>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([C:33]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:34]=2[N:25]=[CH:26][CH:27]=[CH:28]3)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343808-Quinolineboronic acidHCID 68407394HCID 68407394, compound

Product 1

HCID 68406982HCID 68406982, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(2-t-Butoxycarbonylaminophenyl)-4-bromobenzamide (Method 14; 200 mg, 0.5 mmol), 8-quinoline boronic acid (104 mg, 0.6 mmol), tetrakis(triphenylphosphine)palladium (8 mg, 0.007 mmol), 1,2-dimethoxyethane (3 ml) and a saturated aqueous solution of sodium hydrogen carbonate (3 ml) were stirred at 80° C. under an atmosphere of argon for 20 hours. The mixture was allowed to cool before being partitioned between ethyl acetate and water. The organics were washed with brine, dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by flash column chromatography, eluting with methanol/dichloromethane (0-10%), to give the title compound (201 mg, 84%); NMR Spectrum: (DMSO-d6): 1.47 (s, 9H), 7.20 (m, 2H), 7.60 (m, 4H), 7.73 (t, 1H), 7.84 (t, 3H), 8.06 (d, 2H), 8.47 (d, 1H), 8.68 (s, 1H), 8.93 (m, 1H), 9.91 (s, 1H), Mass Spectrum: M+H+: 440.

Workup

  1. temperatureto cool
  2. custombefore being partitioned between ethyl acetate and water
  3. washThe organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by flash column chromatography
  8. washeluting with methanol/dichloromethane (0-10%)

Sources & evidence

ORD record
ord-6f3a225d01a541199b8aa48a9cb5bbd3
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

Loading…