Sodium Carbonate → 5-(4-(4-Fluorobenzamido)phenyl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

HRID 278018Notes

Reaction equation

HRID 278018 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]([NH:27][C:28](=[O:36])[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO.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>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:28]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[NH:10][CH:9]=[C:8]4[CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:22][CH:23]=2)=[O:36])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 531957N-(4-bromophenyl)-4-fluorobenzamideHCID 120418133-(1-Methylpiperidin-4-yl)-1H-Indole-5-Boronic Acid

Product 1

HCID 226267995-(4-(4-Fluorobenzamido)phenyl)-3-(1-Methylpiperidin-4-yl)-1H-IndoleYield 29.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 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-(4-fluorobenzamido)benzene (0.217 g, 0.74 mmol), tetrakis(triphenylphosphine)palladium(0) (0.045 g, 0.039 mol), and 2M aqueous sodium carbonate solution (2 mL) in 15 mL of tetrahydrofuran:methanol (1:1) to give the title compound (0.093 g, 29%) as an amorphous solid. FDMS m/e=427 (M+). EA calculated for C27H26N3OF: C, 75.85; H, 6.13; N, 9.83. Found: C, 75.55; H, 6.18; N, 9.73.

Workup

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

Sources & evidence

ORD record
ord-131909b9d788408da6251f6b3df6b86c
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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