Toluene → HCID 66804072, compound

HRID 1843861Notes

Reaction equation

HRID 1843861 reaction equation
Br[C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH2:9][CH2:10][C:5]=2[S:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C1(C)C=CC=CC=1>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>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:6]3[C:7](=[O:11])[NH:8][CH2:9][CH2:10][C:5]=3[S:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 2856454-Fluorophenylboronic acidHCID 66801867HCID 66801867, compound

Product 1

HCID 66804072HCID 66804072, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Using analogous reaction conditions and workup as described in Example 3, step 5, 3-bromo-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-15b: 300 mg, 1.293 mmol) was reacted with (4-fluoro-phenyl)-dihydroxy-borane (217.11 mg, 1.55 mmol), Pd(PPh3)4 (149.4 mg, 0.1293 mmol), toluene (20 mL) and water (3 mL) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 300 mg of the product (47.02% yield).

Workup

  1. customreaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-e1490e1863bd42a1808a2b91dd36c642
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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