Sodium Carbonate → HCID 24871613, compound

HRID 2106307Notes

Reaction equation

HRID 2106307 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCC2C(=C(OS(C(F)(F)F)(=O)=O)N(C3C=CC=CC=3)N=2)CC1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].S1C=CC=C1B(O)O>CN(C=O)C.O>[C:18]1([N:13]2[C:12]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 67269854HCID 67269854, compoundHCID 86598385HCID 86598385, compound

Product 1

HCID 24871613HCID 24871613, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Phenyl-3-thiophen-2-yl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a solution of 199.8 mg of 2-phenyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 176, Step B) in 3.5 mL of DMF were added 0.6 mL of 2 M aq. Na2CO3 and 75.6 mg of thiophene-2-boronic acid. PdCl2dppf (20.2 mg) was added and the mixture was heated at 80° C. for 16 h. The mixture was poured into water (50 mL) and extracted with CH2Cl2 (3×15 mL) and the combined organic layers were concentrated in vacuo. Chromatography on SiO2 (0 to 50% EtOAc/hexanes) afforded 58.9 mg of the desired compound as a white solid. MS (ESI): exact mass calculated for C22H25N3O2S, 395.17; found, m/z 396.1 [M+H]+.

Workup

  1. extractionextracted with CH2Cl2 (3×15 mL)
  2. concentrationthe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-f3cdddbfc9c44261977f71059d83850a
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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