Potassium Phosphate, Tribasic → HCID 59752684, compound

HRID 599908Notes

Reaction equation

HRID 599908 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:13]=[C:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCC2N(CC3C=CC(Cl)=CC=3)N=C(S(C(F)(F)F)(=O)=O)C=2CC1)=O)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].ClC1C=CC(B(O)O)=CC=1>C1COCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:14]2[C:15]3[CH2:16][CH2:17][NH:8][CH2:9][CH2:10][C:11]=3[C:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:13]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 67269189HCID 67269189, compoundHCID 67269834HCID 67269834, compound

Product 1

HCID 59752684HCID 59752684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Chloro-benzyl)-3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a solution of 142.7 mg of 1-(4-chloro-benzyl)-3-trifluoromethanesulfonyl-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester, prepared as in Example 43, Steps A through C, in 3 mL of THF was added 0.17 g of K3PO4, 54.9 mg of 4-chlorophenylboronic acid, and 22.1 mg of PdCl2dppf. The mixture was heated at reflux for 48 h. The mixture was filtered through diatomaceous earth, rinsing with toluene, and the filtrate was concentrated in vacuo. Chromatography on SiO2 (hexanes to 75% EtOAc/hexanes) afforded 6.7 mg of the desired compound. MS (ESI): exact mass calculated for C25H27Cl2N3O2, 471.15; found, m/z 472.1 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. washrinsing with toluene
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-753a67feab004471ab2a2b8eee80e5ee
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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