N,N,N',N'-Tetramethylethylenediamine → 1-[1-(4-Fluorophenethyl)-piperidin-4-yl]-6-[1-hydroxy-1-(2-methoxypyridin-6-yl)-methyl]indoline

HRID 1790468Notes

Reaction equation

HRID 1790468 reaction equation
CN(C)CCN(C)C.Br[C:10]1[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][CH:11]=1.[F:18][C:19]1[CH:43]=[CH:42][C:22]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[C:39]4[C:34](=[CH:35][CH:36]=[C:37]([CH:40]=[O:41])[CH:38]=4)[CH2:33][CH2:32]3)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1>C(OCC)C>[F:18][C:19]1[CH:43]=[CH:42][C:22]([CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH:28]([N:31]3[C:39]4[C:34](=[CH:35][CH:36]=[C:37]([CH:40]([OH:41])[C:10]5[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][CH:11]=5)[CH:38]=4)[CH2:33][CH2:32]3)[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2568102-Bromo-6-methoxypyridineHCID 220380721-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-formylindoline

Product 1

HCID 220382931-[1-(4-Fluorophenethyl)-piperidin-4-yl]-6-[1-hydroxy-1-(2-methoxypyridin-6-yl)-methyl]indolineYield 76.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Tetramethylethylenediamine (0.26 ml) was added to 6-bromo-2-methoxypyridine (0.32 g) synthesized in accordance with the method described in Tetrahedron, 1373 (1985). and 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindoline (0.4 g) and diethyl ether was employed as the solvent. The resultant mixture was treated as in Example 93 to give the title compound (0.401 g) as colorless crystals (yield: 76.5%).

Workup

  1. customsynthesized in accordance with the method

Sources & evidence

ORD record
ord-72fc3fdffb15443da30650cfd877b0c3
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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