Sodium Bicarbonate → HCID 18707005, compound

HRID 1422104Notes

Reaction equation

HRID 1422104 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][CH2:16][CH3:17])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:35]=[CH:34][C:29]([C:30](=O)[CH2:31]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>>[CH2:16]([C:15]1[C:30]([C:29]2[CH:34]=[CH:35][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)=[CH:31][N:11]2[C:10]=1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH:14][CH:13]=[CH:12]2)[CH3:17]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 18707051HCID 18707051, compound

Product 1

HCID 18707005HCID 18707005, compoundYield 66%

Procedure

3-Benzyloxy-2-propylpyridine was reacted with 4-benzyloxyphenacylbromide and with sodium hydrogen carbonate by the general synthetic principles outlined in example 1, step 2, to afford 1-ethyl-8-benzyloxy-2-(4-benzyloxyphenyl)indolizine as yellow crystals in 66% yield. M.p. 104-105° C. MS(SP): m/z 433 (M+). 1H--NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, 3 H); 2.86 (q, 2 H); 5.12 (s, 2 H); 5.19 (s, 2 H); 6.13 (d, 1 H); 6.38 (t, 1 H); 7.06 (d, 2 H); 7.28-7.54 (m, 13 H); 7.77 (d, 1 H).

Sources & evidence

ORD record
ord-6fc5b959e50e4336937ab45f97c2d71c
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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