5-Ethynylbenzo-1,3-dioxole → Ethyl 3-(2H-1,3-benzodioxol-5-yl)prop-2-ynoate

HRID 24026Notes

Reaction equation

HRID 24026 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)#[CH:2].[C:12]([O:16][C:17](N1C2C(=CC=C(CCOC3C=C4C(=CC=3)NC=C4)N=2)CCC1)=[O:18])(C)(C)[CH3:13]>>[CH2:12]([O:16][C:17](=[O:18])[C:2]#[C:1][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)[CH3:13]

Participants

3

Reactant 2

HCID 926805-Ethynylbenzo-1,3-dioxoleHCID 668210837-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11275992Ethyl 3-(2H-1,3-benzodioxol-5-yl)prop-2-ynoateYield 54%

Procedure

The title compound was synthesized from 5-ethynyl-benzo[1,3]dioxole and 7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester using the procedure described in Example 23, step (c), in 54% yield. 1H NMR (CDCl3) δ 7.16 (dd, 1H, J=1.6, 8.1 Hz), 7.00 (d, 1H, J=1.6 Hz,), 6.80 (d, 1H, J=8.1 Hz,), 6.02 (s, 2H), 4.29 (q, 2H, J=7.2 Hz,), 1.35 (t, 3H, J=7.2 Hz).

Sources & evidence

ORD record
ord-a9e91db964a846f08d7ccdceb8e8220e
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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