1-Benzyloxycarbonyl-4-[5-cyano-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidine → 4-[5-Cyano-1-(2-trimethylsilyl-ethanesulfonyl)indol-3-yl]piperidine

HRID 366503Notes

Reaction equation

HRID 366503 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[N:19]([S:28]([CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])(=[O:30])=[O:29])[CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(OC(N1CCC(C2C3C(=CC=C(F)C=3)NC=2)CC1)=O)(C)(C)C>>[C:26]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:28]([CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])(=[O:29])=[O:30])[CH:18]=[C:17]2[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)#[N:27]

Participants

3

Reactant 2

HCID 226155541-Benzyloxycarbonyl-4-[5-cyano-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidineHCID 227144175-fluoro-3-(1-tert-butoxycarbonylpiperidin-4-yl)-1H-indole

Product 1

HCID 226157214-[5-Cyano-1-(2-trimethylsilyl-ethanesulfonyl)indol-3-yl]piperidine

Procedure

Proceeding as described in Example 19, Step 3, but substituting 1-benzyloxycarbonyl-4-(5-cyano-1-methanesulfonylindol-3-yl)piperidine with 1-benzyloxycarbonyl-4-[5-cyano-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidine (prepared as described in Example 14, Step 2, by substituting 1-benzyloxycarbonyl-4-(5-cyanoindol-3-yl)piperidine for N-tert-butoxycarbonyl-4-(5-fluoroindol-3-yl)piperidine] gave 4-[5-cyano-1-(2-trimethylsilyl-ethanesulfonyl)indol-3-yl]piperidine.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-071e28238a8041ae80ac9ebf4824f694
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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