Sodium Carbonate → HCID 178467438, compound

HRID 2407795Notes

Reaction equation

HRID 2407795 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[S:28][C:27](Br)=[N:26][CH:25]=3)[CH2:19][CH2:18]2)=[O:14])[CH:3]=1.[NH:30]1[CH:34]=[CH:33][C:32](B(O)O)=[N:31]1.C(=O)([O-])[O-].[Na+].[Na+]>COC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:30]1[CH:34]=[CH:33][C:32]([C:27]2[S:28][C:24]([CH2:23][N:20]3[CH2:21][CH2:22][CH:17]([CH2:16][NH:15][C:13](=[O:14])[C:4]4[CH:3]=[C:2]([NH2:1])[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=4)[CH2:18][CH2:19]3)=[CH:25][N:26]=2)=[N:31]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 58504093HCID 58504093, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 178467438HCID 178467438, compoundYield 7.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8254Dimethyl EtherSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of the compound prepared in Example 336 (0.028 g), 1H-pyrazol-3-ylboronic acid (0.013 g) and tetrakis(triphenylphosphine)palladium (0.003 g) in dimethyl ether (0.3 mL) was added a solution of sodium carbonate (0.016 g) in water (0.1 mL). Argon was bubbled through the mixture for 10 minutes. The mixture was then heated at 95° C. for 8 hours. An additional tetrakis(triphenylphosphine)palladium (4.5 mg) and 1H-pyrazol-3-ylboronic acid (13 mg) were added, and the reaction mixture was again purged with argon for 10 minutes and then heated at 110° C. for 6 hours. An additional tetrakis(triphenylphosphine)palladium (10 mg) was added, and the reaction mixture was again purged with argon and then heated at 110° C. for another 38 hours. The reaction mixture was diluted with water and then filtered. The solid was purified by column chromatography on silica gel (dichloromethane:methanol=94:6) to obtain the title compound (2 mg) having the following physical data.

Workup

  1. customArgon was bubbled through the mixture for 10 minutes
  2. additionAn additional tetrakis(triphenylphosphine)palladium (4.5 mg) and 1H-pyrazol-3-ylboronic acid (13 mg) were added
  3. customthe reaction mixture was again purged with argon for 10 minutes
  4. temperatureheated at 110° C. for 6 hours
  5. additionAn additional tetrakis(triphenylphosphine)palladium (10 mg) was added
  6. customthe reaction mixture was again purged with argon
  7. temperatureheated at 110° C. for another 38 hours
  8. additionThe reaction mixture was diluted with water
  9. filtrationfiltered
  10. customThe solid was purified by column chromatography on silica gel (dichloromethane:methanol=94:6)

Sources & evidence

ORD record
ord-b5cd0304770a41d4b6b495e6113e1857
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…