Sodium Carbonate → 5-(Benzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

HRID 278016Notes

Reaction equation

HRID 278016 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.Cl[C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[N:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[NH:25][C:21]=1[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 785722-ChlorobenzimidazoleHCID 120418133-(1-Methylpiperidin-4-yl)-1H-Indole-5-Boronic Acid

Product 1

HCID 120432585-(Benzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-IndoleYield 43%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the procedure of Example 14, beginning with 3-(1-methylpiperidin-4-yl)-1H-indole-5-boronic acid (0.250 g, 0.97 mmol), 2-chlorobenzimidazole (0.140 g, 0.92 mmol), Pd(dppf)Cl2 CH2Cl2 (0.023 g, 0.028 mmol), and 2M aqueous sodium carbonate solution (2 mL) in 6 mL of tetrahydrofuran to give 0.130 g (43%) of the title compound as an amorphous tan solid. FDMS m/e=330 (M+). EA calculated for C21H22N4.¾ H2O C, 73.33; H, 6.89; N, 16.29. Found: C, 73.79; H, 6.66; N, 16.08.

Workup

  1. customThe title compound was prepared by the procedure of Example 14

Sources & evidence

ORD record
ord-b7eafff051304470845e9cad9429fce5
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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