Cyanogen Bromide → HCID 86689157, compound

HRID 1752475Notes

Reaction equation

HRID 1752475 reaction equation
[NH2:1][C@@:2]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([Br:16])[N:10]=1)([CH3:8])[C:3]([F:7])([F:6])[CH2:4][OH:5].C([O-])(O)=O.[Na+].[N:22]#[C:23]Br>CCO>[Br:16][C:11]1[N:10]=[C:9]([C@:2]2([CH3:8])[C:3]([F:6])([F:7])[CH2:4][O:5][C:23]([NH2:22])=[N:1]2)[C:14]([F:15])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 86689160HCID 86689160, compound

Product 1

HCID 86689157HCID 86689157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (R)-3-amino-3-(6-bromo-3-fluoro-pyridin-2-yl)-2,2-difluoro-butan-1-ol (9.49 g, 31.7 mmol) in EtOH (256 ml) was added NaHCO3 (1.066 g, 12.69 mmol) and cyanogen bromide (10.08 g, 95 mmol) and the mixture was warmed to 85° C. over night. After cooling to rt the solvent was evaporated and the residue taken up in 1N HCl and TBME, the layers were separated and the organic layer was washed with 1N HCl. The aq. layers were combined, basified by addition of solid Na2CO3 and extracted with TBME (2×). The combined TBME extracts were washed with sat. aq. NaCl, dried with K2CO3 to provide the desired product as yellow resin. This material was used for the next step without further purification.

Workup

  1. temperatureAfter cooling to rt the solvent
  2. customwas evaporated
  3. customTBME, the layers were separated
  4. washthe organic layer was washed with 1N HCl
  5. additionbasified by addition of solid Na2CO3
  6. extractionextracted with TBME (2×)
  7. washThe combined TBME extracts were washed with sat. aq. NaCl
  8. dry with materialdried with K2CO3

Sources & evidence

ORD record
ord-d728c9d43b8941f2baa7b202ccae53ef
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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