3-Chlorobenzamide → HCID 51037931, compound

HRID 1045812Notes

Reaction equation

HRID 1045812 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N:3]=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:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N: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 51037725HCID 51037725, compound

Product 1

HCID 51037931HCID 51037931, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

Compound 3 (944 mg, 4.55 mmol, 1.00 eq), 3-chlorobenzamide (1.06 g, 6.81 mmol, 1.50 eq), NaOt-Bu (612 mg, 6.37 mmol, 1.40 eq), Pd(OAc)2 (51 mg, 0.23 mmol, 0.050 eq) and Xantphos (263 mg, 0.455 mmol, 0.100 eq) were dissolved in toluene (9.4 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 1.08 g (73%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 11.07 (s, 1H), 9.17 (s, 1H), 8.59 (d, J=2.7 Hz, 1H), 8.46 (dd, J=4.7, 1.2 Hz, 1H), 8.33 (s, 1H), 8.00 (t, J=1.8 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.77 (ddd, J=8.4, 2.8, 1.4 Hz, 1H), 7.67-7.64 (m, 1H), 7.54-7.48 (m, 2H); ES-MS [M+1]+: 327.1.

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-74acc5f0c0154fe0887b24a2b55078d3
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

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