Sodium Carbonate → HCID 22390464, compound

HRID 1071932Notes

Reaction equation

HRID 1071932 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:9][C:8]=1[Cl:23])(=O)=O.[F:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[C:31]([F:33])[CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>C(OCC)C.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(O)C.C1(C)C=CC=CC=1>[ClH:23].[Cl:23][C:8]1[CH:9]=[C:10]([C:13]#[C:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[CH:11]=[CH:12][C:7]=1[C:29]1[CH:28]=[C:27]([F:26])[CH:32]=[C:31]([F:33])[CH:30]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734338(3,5-Difluorophenyl)boronic acid2×HCID 22390451HCID 22390451, compound

Product 1

HCID 22390464HCID 22390464, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

9.5 g of 4-[3-(1-azepanyl)prop-1-ynyl]-2-chlorophenyl trifluoromethanesulphonate (compound Ia.1), 5 g of 3,5-difluorobenzeneboronic acid (compound 2.1), 31 ml of 2 M aqueous sodium carbonate solution, 2.1 g of lithium chloride, 300 ml of toluene, 100 ml of ethanol and 0.7 g of tetrakis(triphenylphosphine)palladium are stirred for 12 hours at 80° C. under an inert atmosphere. The solvents are evaporated off under reduced pressure and the residue obtained is purified by chromatography on a column of silica gel, eluting with a 99/1 (v/v) toluene/ethanol mixture. The compound obtained is taken up in diethyl ether and hydrochloric acid is bubbled through. The precipitate obtained is filtered off and recrystallized from toluene; m.p.=196° C. (HCl).

Workup

  1. customThe solvents are evaporated off under reduced pressure
  2. customthe residue obtained
  3. customis purified by chromatography on a column of silica gel
  4. washeluting with a 99/1 (v/v) toluene/ethanol mixture
  5. customThe compound obtained
  6. customhydrochloric acid is bubbled through
  7. customThe precipitate obtained
  8. filtrationis filtered off
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e07b639e547f4ea8a61195e8061cd28b
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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