Triethylamine → HCID 58696172, compound

HRID 1674697Notes

Reaction equation

HRID 1674697 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.ClC(Cl)(O[C:24](=[O:30])OC(Cl)(Cl)Cl)Cl.[F:32][C:33]1[CH:38]=[C:37]([B:39]2[O:43][C:42]([CH3:45])([CH3:44])[C:41]([CH3:47])([CH3:46])[O:40]2)[CH:36]=[CH:35][C:34]=1[NH2:48]>C(Cl)Cl.O>[F:32][C:33]1[CH:38]=[C:37]([B:39]2[O:43][C:42]([CH3:44])([CH3:45])[C:41]([CH3:47])([CH3:46])[O:40]2)[CH:36]=[CH:35][C:34]=1[NH:48][C:24]([NH:4][C:3]1[CH:5]=[C:6]([C:9]([F:10])([F:11])[F:12])[CH:7]=[CH:8][C:2]=1[F:1])=[O:30]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 58696172HCID 58696172, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

8.55 g (48 mmol) of 2-fluoro-5-trifluoromethylaniline and 4.8 g (48 mmol) of triethylamine were dissolved in 30 mL of dry DCM and added dropwise to a solution of 4.7 g (16 mmol) of triphosgene in 30 mL of DCM at 5-10° C. Within 20 min TLC indicated full consumption of the starting amine. This mixture was treated dropwise with a solution of 11.3 g (48 mmol) of 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine and 4.8 g of triethylamine in 35 mL of DCM at room temperature. Then the reaction mixture was stirred for 2 h, poured into water, the organic layer was separated and evaporated. The residue was crystallized from 90% EtOH yielding 4.5 g of the target product. Flash column chromatography of the residue obtained from evaporation of the mother liquid yielded 2.7 g of the target material (combined yield 7.2 g; 34%).

Workup

  1. customconsumption of the starting amine
  2. customthe organic layer was separated
  3. customevaporated
  4. customThe residue was crystallized from 90% EtOH yielding 4.5 g of the target product
  5. customFlash column chromatography of the residue obtained from evaporation of the mother liquid

Sources & evidence

ORD record
ord-56a335adbbc3452da97140ec78cae79a
Source dataset
uspto-grants-2011_08
Patent number
US08003655B2

Reaction notes

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