Triethylamine → HCID 68238986, compound

HRID 468007Notes

Reaction equation

HRID 468007 reaction equation
[CH3:1][C:2]1([CH3:16])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=[CH:12][C:4]=2[CH2:3]1.C(N(CC)CC)C.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[C:27]([C:34]([F:37])([F:36])[F:35])[CH:26]=1>C1COCC1.[Pd].Cl>[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:13][C:10]2[CH:11]=[CH:12][C:4]3[CH2:3][C:2]([CH3:16])([CH3:1])[O:7][B:6]([OH:8])[C:5]=3[CH:9]=2)=[O:30])=[C:27]([C:34]([F:35])([F:36])[F:37])[CH:26]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 67403353HCID 67403353, compound

Product 1

HCID 68238986HCID 68238986, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3-dimethyl-7-nitro-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol (80 mg, 0.36 mmol) in dry THF (8 mL) was passed through a Thales Nano H-Cube hydrogenator (10% Pd/C catalyst, 1 mL/min flow rate, 1 atm, 30° C.), flushing with an additional 2 mL of THF. To the reaction solution was then added an excess of triethylamine (0.3 mL) and 4-fluoro-2-trifluoromethylbenzoyl chloride (100 mg, 0.44 mmol). The reaction was stirred at room temperature for 16 hours, and then diluted with aqueous hydrochloric acid (10 mL, 1 M). After vigorous mixing, the mixture was extracted with EtOAc (3×5 mL). The combined organic portions were dried over magnesium sulfate and concentrated to dryness. The crude product was purified by silica gel chromatography to produce the title compound as a white solid. LCMS (M/Z): 382 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (s, 6H) 2.83 (s, 2H) 7.14 (d, J=8.4 Hz, 1H) 7.55-7.73 (m, 2H) 7.71-7.86 (m, 2H) 7.90 (d, J=2.3 Hz, 1H) 8.35 (s, 1H) 10.47 (s, 1H).

Workup

  1. customflushing with an additional 2 mL of THF
  2. extractionAfter vigorous mixing, the mixture was extracted with EtOAc (3×5 mL)
  3. dry with materialThe combined organic portions were dried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2f84ade5fbef4fd6bb1603029fe6b38a
Source dataset
uspto-grants-2014_01
Patent number
US08623911B2

Reaction notes

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