Sodium Bicarbonate → HCID 59415861, compound

HRID 2061823Notes

Reaction equation

HRID 2061823 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11](I)=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6]1.[CH:23]([NH:26][C:27](=[O:47])[NH:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[C:31]([C:38]2[S:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[N:42]=2)[CH:30]=1)([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:32]3[CH:33]=[N:34][C:29]([NH:28][C:27]([NH:26][CH:23]([CH3:25])[CH3:24])=[O:47])=[CH:30][C:31]=3[C:38]3[S:39][CH:40]=[C:41]([C:43]([F:46])([F:44])[F:45])[N:42]=3)=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 57765323HCID 57765323, compound2×HCID 59415742HCID 59415742, compound2×

Product 1

HCID 59415861HCID 59415861, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of ethyl 1-(2-(dimethylamino)ethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 29, 250 mg, 0.60 mmol) in dimethoxyethane (4.8 mL) in a microwave vial was stirred with heating to obtain a solution. The solution was then cooled to 30° C., trans-dichlorobis(triphenylphosphine)palladium (II) (55 mg, 0.08 mmol) was added and the mixture was stirred for 10 min at room temperature. 6-(3-isopropylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 89, 294 mg, 0.79 mmol) was added to the mixture followed by an aqueous solution of sodium bicarbonate (163 mg in 1.2 mL of water) and the vial was sealed. The mixture was stirred at 65° C. for 30 min in a heating block then cooled to room temperature. The crude reaction mixture was placed into fridge for a 2 h. The solid precipitate that formed was collected by filtration, washed with a small amount of dimethoxyethane, methyl tert-butyl ether and dried to give ˜270 mg yellowish solid.

Workup

  1. temperaturewith heating
  2. customto obtain a solution
  3. stirringthe mixture was stirred for 10 min at room temperature
  4. customthe vial was sealed
  5. stirringThe mixture was stirred at 65° C. for 30 min in a heating block
  6. temperaturethen cooled to room temperature
  7. customThe crude reaction mixture
  8. customThe solid precipitate that formed
  9. filtrationwas collected by filtration
  10. washwashed with a small amount of dimethoxyethane, methyl tert-butyl ether
  11. customdried

Sources & evidence

ORD record
ord-28e8f519bcee429a9aff41aa29e7e032
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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