Oxalyl chloride → HCID 89907782, compound

HRID 629101Notes

Reaction equation

HRID 629101 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[C:9]([F:17])=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=O.[F:18][C:19]([F:29])([F:28])[O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[Br:7][C:8]1[C:9]([F:17])=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH:25][C:24]1[CH:26]=[CH:27][C:21]([O:20][C:19]([F:18])([F:28])[F:29])=[CH:22][CH:23]=1)=[O:13]

Participants

8

Reactant 5

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 89907782HCID 89907782, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (0.657 mL, 7.50 mmol) in DCM (10 mL) and of DMF (0.01 mL) were added to a suspension of 3-bromo-2-fluorobenzoic acid (1.095 g, 5 mmol) in DCM (10 mL) and the RM was stirred for at RT for 2 h. The solvent was evaporated off under reduced pressure. The residue was dissolved in DCE (10 mL), treated dropwise with a solution of 4-(trifluoromethoxy)aniline (0.744 mL, 5.50 mmol) and DIPEA (1.747 mL, 10.00 mmol) and the RM was stirred for at RT for 1 h. The RM was treated with an aq. NaHCO3 and extracted with DCM. The combined extracts were washed with water, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 100 g, n-hexane/EtOAc 2:1) to afford the title compound as beige crystals. UPLC-MS (Condition 2) tR=1.22 min, m/z=375.9/378.0 [M−H−]−.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. dissolutionThe residue was dissolved in DCE (10 mL)
  3. stirringthe RM was stirred for at RT for 1 h
  4. extractionextracted with DCM
  5. washThe combined extracts were washed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customto give the crude product which
  9. customwas purified by flash chromatography (Silica gel column, 100 g, n-hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-ea288e1de56544f49a1dbdc7c2c1e38c
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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