p-Bromoacetophenone → HCID 9797677, compound

HRID 278020Notes

Reaction equation

HRID 278020 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][CH:9]=[C:8]3[CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:22][CH:23]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 7466p-BromoacetophenoneHCID 10340Sodium CarbonateHCID 120418133-(1-Methylpiperidin-4-yl)-1H-Indole-5-Boronic Acid

Product 1

HCID 9797677HCID 9797677, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The title compound was prepared by the procedure of Example 10, beginning with 3-(1-methylpiperidin-4-yl)-1H-indole-5-boronic acid (0.200 g, 0.77 mmol), 1-bromo-4-acetylbenzene (0.147 g, 0.74 mmol), tetrakis(triphenylphosphine)palladium(O) (0.045 g, 0.039 mmol), and 2M aqueous sodium carbonate solution (2 mL) in 15 mL of tetrahydrofuran:methanol (1:1) to give the title compound (0.171 g, 70%) as an amorphous solid. FDMS m/e=348 (M+). EA calculated for C22H24N2O.¼ H2O: C, 78.19; H, 7.31; N, 8.29. Found: C, 78.00; H, 7.27; N, 7.93.

Workup

  1. customThe title compound was prepared by the procedure of Example 10

Sources & evidence

ORD record
ord-00130e22f3d44fe3a05bafc9acc589cc
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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