Sodium Carbonate → HCID 89714886, compound

HRID 2273071Notes

Reaction equation

HRID 2273071 reaction equation
Cl[C:2]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH3:15])[CH2:9][C:8]([CH3:17])([CH3:16])[O:7][C:6]=2[N:5]=[C:4]([S:18][CH3:19])[N:3]=1.[C:20]([O:24][C:25](=[O:43])[NH:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[C:29]([F:42])[CH:28]=1)([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([O:24][C:25](=[O:43])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[C:12]3[C:11](=[O:13])[N:10]([CH2:14][CH3:15])[CH2:9][C:8]([CH3:17])([CH3:16])[O:7][C:6]=3[N:5]=[C:4]([S:18][CH3:19])[N:3]=2)=[C:29]([F:42])[CH:28]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 59578631HCID 59578631, compoundHCID 89714606HCID 89714606, compound

Product 1

HCID 89714886HCID 89714886, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

1.77 g (5.85 mmol) of 4-chloro-6-ethyl-8,8-dimethyl-2-methylsulfanyl-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one, 2.27 g (6.73 mmol) of [3-fluoro-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]carbamic acid tert-butyl ester and 14.63 ml of a 2 M solution of Na2CO3 in 35 ml dioxane are mixed together, followed by degassing 5 times with argon. 339 mg (293 μmol) of tetrakis(triphenylphosphine)palladium (0) are added and the mixture is degassed a further 3 times with argon and then heated at 90° C. for 2 hours 30 minutes. The resulting mixture is allowed to cool. It is poured into water. The product is filtered off, washed with water, dissolved in DCM, dried and concentrated. It is taken up in Et2O, and the mixture is stirred, filtered and dried. 2.94 g of [4-(6-ethyl-8,8-dimethyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclo hepten-4-yl)-3-fluorophenyl]carbamic acid tert-butyl ester are recovered.

Workup

  1. customby degassing 5 times with argon
  2. customthe mixture is degassed a further 3 times with argon
  3. temperatureto cool
  4. additionIt is poured into water
  5. filtrationThe product is filtered off
  6. washwashed with water
  7. dissolutiondissolved in DCM
  8. customdried
  9. concentrationconcentrated
  10. filtrationfiltered
  11. customdried
  12. custom2.94 g of [4-(6-ethyl-8,8-dimethyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclo hepten-4-yl)-3-fluorophenyl]carbamic acid tert-butyl ester are recovered

Sources & evidence

ORD record
ord-c4ff609c115948698179c438f97570a9
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

Loading…