3-Chlorobenzamide → HCID 52913684, compound

HRID 1887461Notes

Reaction equation

HRID 1887461 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:9]([CH3:16])[C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([NH2:23])=[O:22].CC([O-])(C)C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([NH:23][C:2]1[CH:3]=[C:4]([N:9]([CH3:16])[C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1)=[O:22]

Participants

7

Reactant 4

HCID 692543-ChlorobenzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 58337588HCID 58337588, compound

Product 1

HCID 52913684HCID 52913684, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Compound 35 (59 mg, 0.20 mmol, 1.0 eq), 3-chlorobenzamide (46 mg, 0.30 mmol, 1.5 eq), NaOt-Bu (27 mg, 0.28 mmol, 1.4 eq), Pd(OAc)2 (2.2 mg, 0.0098 mmol, 0.050 eq) and Xantphos (11.4 mg, 0.0197 mmol, 0.100 eq) were dissolved in toluene (1 mL) in a microwave vial. The vial was purged with argon, capped, and heated at 110° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 42 mg (57%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 8.8 (s, 1H), 8.6 (s, 2H), 7.96 (t, J=1.8 Hz, 1H), 7.97-7.85 (m, 1H), 7.67-7.65 (m, 2H), 7.55 (t, J=7.8 Hz, 1H), 7.41 (t, J=1.9 Hz, 1H), 6.95 (t, J=2.0 Hz, 1H), 3.34 (s, 3H); [M+1]+: 373.1.

Workup

  1. customThe vial was purged with argon
  2. customcapped
  3. temperatureAfter cooling the reaction
  4. filtrationwas filtered over a plug of celite
  5. washthe plug was washed with 5% MeOH/CH2Cl2
  6. customThe solvents were removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-72ad2fb5bb6840d3a1c675cfe2996203
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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