Sodium Carbonate → HCID 57520684, compound

HRID 1403078Notes

Reaction equation

HRID 1403078 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:16]=[C:15]([C:17]3[C:26]4[C:21](=[C:22](B5OC(C)(C)C(C)(C)O5)[CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][N:18]=3)[CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH2:4][CH2:3]1.[NH2:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41](Br)[CH:42]=1.C(=O)([O-])[O-:45].[Na+].[Na+]>COCCOC.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>[NH2:36][C:37]1[CH:42]=[C:41]([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:21]=2[CH:20]=[CH:19][N:18]=[C:17]3[C:15]2[CH:14]=[CH:13][C:10]([C:11]([NH2:12])=[O:45])=[C:9]([NH:8][CH:5]3[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]3)[CH:16]=2)[CH:40]=[N:39][CH:38]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 8176813-Amino-5-bromopyridineHCID 89886791HCID 89886791, compound

Product 1

HCID 57520684HCID 57520684, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Pd(PPh3)4 (0.013 g) was added to a solution of compound (2b) (0.102 g), 3-amino-5-bromopyridine (0.042 g), and an aqueous sodium carbonate solution (2 M, 1.5 mL) in ethylene glycol dimethyl ether (3 mL) in a nitrogen atmosphere, and the mixture was stirred at 85° C. for 3 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off. An aqueous sodium hydroxide solution (4 M, 0.093 mL) and a 300 aqueous hydrogen peroxide solution (0.045 mL) were added to a solution of the obtained residue in DMSO (3 mL) and ethanol (1.5 mL) at room temperature, and the mixture was stirred for 30 minutes. Water was added to the reaction solution, and the deposit was collected by filtration, then washed with water and ether by sprinkling, and then dried under reduced pressure to obtain compound (2) (0.045 g, yield based on 2 steps: 45%) as a pale yellow solid.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. additionAn aqueous sodium hydroxide solution (4 M, 0.093 mL) and a 300 aqueous hydrogen peroxide solution (0.045 mL) were added to a solution of the obtained residue in DMSO (3 mL)
  6. additionWater was added to the reaction solution
  7. filtrationthe deposit was collected by filtration
  8. washwashed with water and ether by sprinkling
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-eebdfcac9ca644caa3fd43584dafdca3
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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