Sodium Carbonate → HCID 11675896, compound

HRID 1173836Notes

Reaction equation

HRID 1173836 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[S:6][C:7]([CH2:9][CH:10]3[CH2:14][CH2:13][N:12]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[C:11]3=[O:21])=[CH:8][C:4]=2[CH:3]=1.[F:24][C:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[CH:27][N:26]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>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.O.O1CCOCC1>[CH:15]1([N:12]2[CH2:13][CH2:14][CH:10]([CH2:9][C:7]3[S:6][C:5]4[CH:22]=[CH:23][C:2]([C:29]5[CH:28]=[CH:27][N:26]=[C:25]([F:24])[CH:30]=5)=[CH:3][C:4]=4[CH:8]=3)[C:11]2=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27833962-Fluoropyridine-4-boronic acidHCID 11710884HCID 11710884, compound

Product 1

HCID 11675896HCID 11675896, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Add 3-(5-bromo-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (250 mg, 0.64 mmol), 2-fluoropyridine-4-boronic acid (200 mg, 1 mmol), LiCl (10 eq) and Pd(PPh3)4 (0.05 eq) into a solution of dioxane (10 mL) and 2M Na2CO3 (2 mL) and heat at 80° C. for 1 hour. Pour the reaction mixture into water and extract with ethyl acetate. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-50% ethyl acetate in hexanes) to give the title compound as a pale yellow powder (260 mg, 58%): MS (APCI-pos mode) m/z (rel intensity): 409.2 (M+H, 100%).

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by silica gel (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-06c0c38f10894d329397b6b084cacf7e
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

Loading…