Sodium Carbonate → HCID 11427352, compound

HRID 1694727Notes

Reaction equation

HRID 1694727 reaction equation
B([C:4]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9])(O)O.[NH2:19][C:20]1[C:25](Br)=[CH:24][C:23]([CH3:27])=[CH:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.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>[NH2:19][C:20]1[C:25]([C:4]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:5]=2[O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:24][C:23]([CH3:27])=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5193802-Amino-3-bromo-5-methylpyridineHCID 70654069[2-Borono-4-(trifluoromethyl)phenoxy]-acetic acid

Product 1

HCID 11427352HCID 11427352, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from step (iv) (0.1 g), 2-amino-3-bromo-5-methylpyridine (0.071 g), tetrakis(triphenylphosphine)palladium(0) (0.046 g), sodium carbonate (0.12 g) in methanol (2 ml) was heated in a CEM microwave (variable wattage up to 150 W) at 100° C. for 10 min. The mixture was loaded onto SCX resin (sulphonic acid resin), flushed with methanol then the product eluted with methanol/ammonia. The methanol/ammonia filtrate was evaporated under reduced pressure then loaded onto bondelut-NH2 resin. The resin was flushed with methanol then the product eluted with methanol/acetic acid. The methanol/acetic acid filtrate was evaporated and the residue purified by RPHPLC. Yield 0.089 g

Workup

  1. customflushed with methanol
  2. washthe product eluted with methanol/ammonia
  3. customThe methanol/ammonia filtrate was evaporated under reduced pressure
  4. customThe resin was flushed with methanol
  5. washthe product eluted with methanol/acetic acid
  6. customThe methanol/acetic acid filtrate was evaporated
  7. customthe residue purified by RPHPLC

Sources & evidence

ORD record
ord-ac44c77e02b243c3affb7de28935d62f
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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