Sodium bis(trimethylsilyl)amide → HCID 135476514, compound

HRID 2245575Notes

Reaction equation

HRID 2245575 reaction equation
[Cl:1][C:2]1[N+:7]([O-])=[CH:6][C:5]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[O:16]=[C:17]1[CH2:25][C:24]2[C:19](=[CH:20][C:21]([C:26]#[N:27])=[CH:22][CH:23]=2)[NH:18]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>>[ClH:1].[OH:16][C:17]1[NH:18][C:19]2[C:24]([C:25]=1[C:2]1[CH:3]=[CH:4][C:5]([CH2:9][N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:6][N:7]=1)=[CH:23][CH:22]=[C:21]([C:26]#[N:27])[CH:20]=2

Participants

4

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27733482-Oxindole-6-carbonitrileHCID 85873063HCID 85873063, compound

Product 1

HCID 135476514HCID 135476514, compound

Procedure

The title compound was prepared as described for Example 117. Starting material: 1-[(6-chloro-1-oxidopyridin-3-yl)methyl]piperidine (0.136 g, 0.60 mmol) and 2-oxoindoline-6-carbonitrile (0.100 g, 0.63 mmol) and sodium bis(trimethylsilyl)amide (1.4 mL, 1.4 mmol). Yield: 0.031 g, 12%: 1H NMR D2O, 400 MHz) δ 8.01 (d, J=2 Hz, 1H), 7.75 (dd, J=9, 2 Hz, 1H), 7.28 (d, J=9 Hz, 1H), 7.06 (m, 2H), 6.92 (s, 1H), 4.19 (s, 2H), 3.53 (m, 2H), 2.98 (m, 2H), 1.94 (s, 2H), 1.82 (m, 1H), 1.70 (m, 2H), 1.46 (m, 1H); MS (ESP) m/z 349 (M++1).

Sources & evidence

ORD record
ord-8537ec1dc95c453d84421ddaab11f98c
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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