Bromine → HCID 57566613, compound

HRID 217151Notes

Reaction equation

HRID 217151 reaction equation
[F:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:21]Br>C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:21][C:12]1[CH:11]=[CH:10][C:9]([NH:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])=[C:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 11065575N-[2-(3-Fluoropyridin-2-yl)phenyl]-2,2-dimethylpropanamide

Product 1

HCID 57566613HCID 57566613, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 24477Sodium ThiosulfateSolvent

Procedure

To a room temperature suspension of N-[2-(3-fluoro-pyridin-2-yl)-phenyl]-2,2-dimethyl-propionamide (˜77 mmoles) in acetic acid (300 mL) was added bromine (12 mL, 228 mmoles) as a solution in 50 mL of acetic acid over a 1 hour period. The heterogenous mixture was stirred at room temperature for 5 hours over which time a thick precipitate formed. The mixture was then poured over ice, diluted with 1N Na2S2O3 (500 mL), and stirred for 1 hour. The solids were filtered, re-suspended in water (2 L), stirred for 1 hour, then filtered and washed with water again. The resulting solids were pumped to dryness at 50° C., re-suspended in HOAc (400 mL), and treated with bromine (4 mL, 76 mmoles) in acetic acid solution (20 mL) over a 20 minute period. The resulting heterogenous mixture was stirred for 5 hours, then quenched and treated as described above. The resulting solids were vacuum dried at 50° C. to afford the title compound (19.1 grams, 72%) as a tan powder.

Workup

  1. customformed
  2. additionThe mixture was then poured over ice
  3. stirringstirred for 1 hour
  4. filtrationThe solids were filtered
  5. stirringstirred for 1 hour
  6. filtrationfiltered
  7. washwashed with water again
  8. customwere pumped to dryness at 50° C.
  9. stirringThe resulting heterogenous mixture was stirred for 5 hours
  10. customquenched
  11. additiontreated
  12. customdried at 50° C.

Sources & evidence

ORD record
ord-1437c4d46bcf413a8015cfc4295493ea
Source dataset
uspto-grants-2012_06
Patent number
US08193352B2

Reaction notes

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