Tert-Butylamine → HCID 22336251, compound

HRID 2175790Notes

Reaction equation

HRID 2175790 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].C(Cl)(=O)C(Cl)=O.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C=O)C.Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:8])=[CH:4][C:3]=1[F:11]

Participants

7

Reactant 3

HCID 6385Tert-ButylamineHCID 65578Oxalyl chlorideHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 22336251HCID 22336251, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-bromo-3-fluorobenzoic acid (19 g, 87 mmol) in DCM (200 mL) was added oxalyl chloride (9.10 mL, 104 mmol), followed by 1 drop of DMF. The mixture was allowed to stir at rt for 2 h. Upon clarification of the suspension, the solution was concentrated to dryness. The residue was redissolved in DCM (200 mL) and cooled to 0° C. Next the solution was treated with TEA (30.2 mL, 217 mmol) followed by tert-butyl amine (12.0 mL, 113 mmol). The solution was allowed to stir for 12 h. The reaction was diluted with 1N HCl (200 mL). The organic layer was then removed and washed with 1N NaOH. The organic layer was dried over MgSO4, filtered and concentrated to afford the title compound.

Workup

  1. concentrationUpon clarification of the suspension, the solution was concentrated to dryness
  2. dissolutionThe residue was redissolved in DCM (200 mL)
  3. temperaturecooled to 0° C
  4. stirringto stir for 12 h
  5. customThe organic layer was then removed
  6. washwashed with 1N NaOH
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b52cb16fa6fd435fa2e926648cf6069d
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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