Toluene → HCID 24957866, compound

HRID 502251Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:22]#[N:23])=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=3)[N:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1.BrC1C=C2C(C=CN2)=CC=1.[C:34]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.ClCCl>[C:37]([O:36][C:34]([N:41]1[CH2:46][CH2:45][N:44]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([C:22]#[N:23])=[C:7]([C:13]4[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=4)[N:8]3[CH2:11][CH3:12])=[CH:4][CH:3]=2)[CH2:43][CH2:42]1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

Conditions

Temperature: 80 °C

Procedure

6-Bromo-2-(4-ethoxyphenyl)-1-ethyl-indole-3-carbonitrile (0.37 g, 1.0 mmol), prepared from 6-bromoindole using the procedure described in example 1Gb, is mixed with NaO t-Bu (0.13 g, 1.4 mmol), Pd2(dba)3 (0.009 g, 0.01 mmol), BINAP (0.019 g, 0.03 mmol), 1-Boc-piperazine (0.22 g, 1.2 mmol) and dry toluene (3.0 mL). The mixture is stirred at 80° C. for 6 h. After cooling, the solvent is replaced with dichloromethane and chromatographed (silica gel, DCM/EtOAc, 9.5/0.5) to provide 4-[3-cyano-2-(4-ethoxyphenyl)-1-ethylindol-6-yl]piperazine-1-carboxylic acid tert-butyl ester (0.41 g, 86%).

Workup

temperatureAfter cooling
customchromatographed (silica gel, DCM/EtOAc, 9.5/0.5)

Sources & evidence

ORD record: ord-f5e3632be4c14dca846754d04ef12fc7
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772271B2

Reaction notes

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