3-Chlorobenzamide → HCID 58337495, compound

HRID 1887444Notes

Reaction equation

HRID 1887444 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH2:22])=[O:21].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:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH:22][C:2]1[CH:3]=[C:4]([O:5][C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:12]=[C:13]([Cl:15])[CH:14]=1)=[O:21]

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 58337714HCID 58337714, compound

Product 1

HCID 58337495HCID 58337495, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Compound 11 (1.0 g, 3.5 mmol, 1.0 eq), 3-chlorobenzamide (820 mg, 5.27 mmol, 1.50 eq), NaOt-Bu (473 mg, 4.92 mmol, 1.40 eq), Pd(OAc)2 (40 mg, 0.18 mmol, 0.050 eq) and Xantphos (203 mg, 0.351 mmol, 0.100 eq) were dissolved in toluene (15 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 921 mg (73%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.5 (s, 1H), 8.47 (d, J=2.8 Hz, 1H), 8.45 (dd, J=4.6, 1.3 Hz, 1H), 7.95 (t, J=1.8 Hz, 1H), 7.86 (dt, J=7.8, 1.3 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.67 (dq, J=8.1, 1.2 Hz, 1H), 7.58 (ddd, J=8.4, 2.9, 1.4 Hz, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.49 (dd, J=8.4, 4.7, 1H), 7.40 (t, J=2.1 Hz, 1H), 6.94 (t, J=2.1 Hz, 1H); [M+1]+: 359.2.

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-e59ec563120c4eecacc04727f0fa7bd5
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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