HCID 10883437, compound → HCID 54415132, compound

HRID 1422070Notes

Reaction equation

HRID 1422070 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3=[CH:24][C:25]([CH2:26][OH:27])=[C:21]4[N:22]3[C:17](=[CH:18][CH:19]=[CH:20]4)[C:16]=2[CH2:28][CH3:29])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][N:31]([CH3:40])[C:32](=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br>>[CH3:30][N:31]([CH3:40])[C:32](=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:27][CH2:26][C:25]1[CH:24]=[C:23]2[N:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=13)[C:16]([CH2:28][CH3:29])=[C:15]2[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 10883437HCID 10883437, compoundHCID 10944045HCID 10944045, compound

Product 1

HCID 54415132HCID 54415132, compoundYield 31%

Procedure

2-(4-Benzyloxyphenyl)-1-ethyl-4-hydroxymethylpyrrolo[2,1,5-cd]indolizine was alkylated, using 6-bromohexanoic acid dimethylamide as the alkylating agent, by the general synthetic principle outlined in Example 5, to afford 6-[2-(4-benzyloxyphenyl)-1-ethylpyrrolo[2,1,5-cd]indolizin-4-ylmethoxy]hexanoic acid dimethylamide as a yellow oil in 31% yield. 1H-NMR (CDCl3, 300 MHz) δ: 1.37-1.50 (m, 5H); 160-1.71 (m, 4H); 2.28 (t, 2H); 2.91 (s, 3H); 2.93 (s, 3H); 3.24 (q, 2H); 3.56 (t, 2H); 5.01 (s, 2H); 5.17 (s, 2H); 7.15 (d, 2H); 7.32-7.54 (m, 6H); 7.63 (t, 1H); 7.73 (d, 2H); 7.90 (d, 1H); 7.99 (d, 1H).

Sources & evidence

ORD record
ord-09429418119d405ba8c841176123e7c9
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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