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

HRID 278017Notes

Reaction equation

HRID 278017 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[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23](C(OC(C)(C)C)=O)[N:22]=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>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[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)=[N:22]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 120418133-(1-Methylpiperidin-4-yl)-1H-Indole-5-Boronic AcidHCID 22626787Tert-butyl 3-chloroindazole-1-carboxylate

Product 1

HCID 120418085-(Indazol-3-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

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), 3-chloro-1-(tert-butoxycarbonyl)indazole (0.230 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 0.197 g (47%) of 5-(3-[1-tert-butoxycarbonyl]indazolyl)-3-(1-methylpiperidin-4-yl)-1H-indole as an amorphous tan solid, which was dissolved in 3 mL of tetrahydrofuran, followed by the addition of sodium methoxide (0.074 g, 1.38 mmol) in 1 mL of methanol, and the mixture was allowed to stir at room temperature for 0.5 hours, followed by extractive work-up and silica gel chromatography to give 0.062 g (54%) of the title compound as an amorphous off-white solid. FDMS m/e=330 (M+). EA calculated for C21H22N4.½ H2O C, 74.31; H, 6.83; N, 16.50. Found: C, 74.52; H, 6.96; N, 15.95.

Sources & evidence

ORD record
ord-a0af63ae2c984e4f9884d6b3635f718b
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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