Sodium Carbonate → 2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol

HRID 1916710Notes

Reaction equation

C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]3)=[N:12][CH:13]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][CH:30]=1>O1CCOCC1.CO>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]4)=[N:12][CH:13]=2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Under an N2 atmosphere 56 mL 2 M Na2CO3 solution and 1.29 g (1.1 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 19.0 g (55.7 mmol) 2-[5-(5-bromo-pyridin-2-ylethynyl)-indol-1-yl]-ethanol and 11.55 g (72.4 mmol) 4-chlorophenyl-boric acid in 320 mL 1,4-dioxane and 80 mL MeOH and the reaction mixture is heated to 110° C. for 16 h. The mixture is evaporated down i. vac., the residue is combined with 300 mL water and the suspension is stirred vigorously. The precipitate is filtered off and washed with 200 mL water. The precipitate is suspended three times, each time with 600 mL PE/DCM (5:1), suction filtered and finally dried in the air until a constant weight is obtained.

Workup

customThe mixture is evaporated down i
filtrationThe precipitate is filtered off
washwashed with 200 mL water
filtrationeach time with 600 mL PE/DCM (5:1), suction filtered
customfinally dried in the air until a constant weight
customis obtained

Sources & evidence

ORD record: ord-9ea2b469ed1b4fe1a1b90051c789402f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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