Hydrochloric Acid → HCID 89714569, compound

HRID 2273065Notes

Reaction equation

HRID 2273065 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[CH:4][C:3]=1[F:17].[CH2:18]([N:20]([CH2:23]C)CC)[CH3:19].ClC(Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.C(N)C.C([O-])([O-])=O.[K+].[K+].Cl>C(Cl)Cl>[CH2:18]([NH:20][C:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:9][C:10]([CH3:12])([CH3:11])[C:13]([CH3:15])([CH3:14])[O:16]2)=[CH:4][C:3]=1[F:17])=[O:28])[CH3:19]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 94429TriphosgeneHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 89714569HCID 89714569, compoundYield 204.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

5 g of 4-amino-3-fluorophenylboronic acid pinacol ester (21.08 mmol) are placed in 100 ml of DCM. 3.23 ml of triethylamine (23.20 mmol) are added. The reaction mixture is cooled in an ice bath to 4° C. After stirring for 5 minutes, 2.21 g of triphosgene (7.38 mmol) are added portionwise, and the ice bath is then removed. After stirring for 1 hour 30 minutes at room temperature, 8.77 g of ethylamine hydrochloride (105.45 mmol) and then 14.57 g of K2CO3 (105.45 mmol) are added portionwise. After 2 hours, the medium is cooled in an ice bath and then acidified with 1 N hydrochloric acid solution. The aqueous phase is extracted 3 times with DCM. The organic phases are combined, washed with brine, dried over MgSO4, filtered and concentrated. The residue is chromatographed on silica gel with a gradient of from 0% to 5% MeOH in DCM to give 4.65 g of 1-ethyl-3-[2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]urea.

Workup

  1. customthe ice bath is then removed
  2. stirringAfter stirring for 1 hour 30 minutes at room temperature
  3. waitAfter 2 hours
  4. temperaturethe medium is cooled in an ice bath
  5. extractionThe aqueous phase is extracted 3 times with DCM
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is chromatographed on silica gel with a gradient of from 0% to 5% MeOH in DCM

Sources & evidence

ORD record
ord-5866cf8379e2486b98418ae31c2ddfdc
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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