Hydrochloric Acid → HCID 58277323, compound

HRID 1949257Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=3)[N:12]=[C:11]([C:22]([O:24]CC)=[O:23])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-:27].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.Cl>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:16]1[CH:15]=[C:14]([N:13]2[C:9]([C:4]3[CH:3]=[C:2]([OH:27])[CH:7]=[C:6]([F:8])[CH:5]=3)=[CH:10][C:11]([C:22]([OH:24])=[O:23])=[N:12]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

Conditions

Temperature: 80 °C

Procedure

200 mg (0.453 mmol) of the compound of Example 52A are provided in a mixture of 1.5 ml of 1,4-dioxane and 0.9 ml of degassed water under argon, 152 mg (2.72 mmol) of potassium hydroxide, 23.1 mg (0.054 mmol) of 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl and 16.6 mg (0.018 mmol) of tris(dibenzylideneacetone)dipalladium(0) are added, and the mixture is heated at 80° C. overnight. A 1N aqueous hydrogen chloride solution is subsequently added until the pH is acidic, and the reaction mixture is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). 100 mg (63% of theory) of the title compound are obtained.

Workup

customthe reaction mixture is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-5a5db71382e4456d9a1eeb5b9462e6df
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399682B2

Reaction notes

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