3-Chlorobenzamide → HCID 50992438, compound

HRID 1887446Notes

Reaction equation

HRID 1887446 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][C:6]1[CH:7]=[N:8][CH:9]=[N:10][CH:11]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20].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.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH:21][C:2]1[CH:14]=[CH:13][CH:12]=[C:4]([O:5][C:6]2[CH:7]=[N:8][CH:9]=[N:10][CH:11]=2)[CH:3]=1)=[O:20]

Participants

8

Reactant 4

HCID 692543-ChlorobenzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 58337756HCID 58337756, compound

Product 1

HCID 50992438HCID 50992438, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

Compound 13 (580 mg, 2.31 mmol, 1.00 eq), 3-chlorobenzamide (539 mg, 3.46 mmol, 1.50 eq), NaOt-Bu (311 mg, 3.24 mmol, 1.40 eq), Pd(OAc)2 (26 mg, 0.12 mmol, 0.050 eq) and Xantphos (134 mg, 0.232 mmol, 0.100 eq) were dissolved in toluene (6 mL) in a flame-dried sealed tube and heated at 110° C. for 18 h. The reaction was cooled to rt, diluted with CH2Cl2 and filtered through a plug of celite. Purification by flash chromatography on silica gel afforded 68 mg (9%) of the title compound as an off white semi-solid: 1H NMR (400 MHz, DMSO-d6) δ 10.44 (s, 1H), 9.03 (s, 1H), 8.68 (s, 2H), 7.97 (t, J=1.6 Hz, 1H), 7.88 (d, J=7.8 Hz, 1H), 7.65 (t, J=9.8 Hz, 2H), 7.59 (t, J=2.0 Hz, 1H), 7.56 (t, J=7.8 Hz, 1H), 7.42 (t, J=8.2 Hz, 1H), 6.91 (dd, J=8.1, 1.9 Hz, 1H); ES-MS [M+1]+: 326.1.

Workup

  1. customsealed tube
  2. temperatureThe reaction was cooled to rt
  3. filtrationfiltered through a plug of celite
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-651c20aa4a524fc8ba88e2a14abbf1cd
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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