Potassium Carbonate → HCID 59752641, compound

HRID 749734Notes

Reaction equation

HRID 749734 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][CH:29]=[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.C([O-])([O-])=O.[K+].[K+].C1(B(O)O)C=CC=CC=1>C1COCC1.O>[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:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[N:13]2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 67269189HCID 67269189, compoundHCID 67269421HCID 67269421, compound

Product 1

HCID 59752641HCID 59752641, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-Chloro-benzyl)-3-phenyl-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a solution of 0.13 g 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 300 μL of water, 0.11 g of K2CO3, 44.9 mg of phenylboronic acid, and 20.0 mg of PdCl2dppf. The mixture was heated at 100° C. for 18 h. The mixture was filtered through diatomaceous earth and concentrated in vacuo. Chromatography on SiO2 (hexanes to 45% EtOAc/hexanes) afforded 16.1 mg of the desired compound. MS (ESI): exact mass calculated for C25H28ClN3O2, 437.19; found, m/z 438.2 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eec32faa8ef140edbac550c84c95816e
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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