1,3-Dichloro-2-(prop-2-yn-1-yloxy)benzene → (7-{5-[(2,6-dichlorophenoxy)methyl]-1H-1,2,3-triazol-1-yl}-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetic acid

HRID 570640Notes

Reaction equation

HRID 570640 reaction equation
[N:1]([CH:4]1[CH2:23][N:8]2[C:9]3[C:14]([C:15]([CH2:16][C:17]([O:19]CCC)=[O:18])=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N+:2]=[N-:3].[CH2:24]([O:27][C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35])[C:25]#[CH:26]>>[Cl:34][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:35])[C:28]=1[O:27][CH2:24][C:25]1[N:1]([CH:4]2[CH2:23][N:8]3[C:9]4[C:14]([C:15]([CH2:16][C:17]([OH:19])=[O:18])=[C:7]3[CH2:6][CH2:5]2)=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:2]=[N:3][CH:26]=1

Participants

3

Reactant 2

HCID 27768801,3-Dichloro-2-(prop-2-yn-1-yloxy)benzeneHCID 59487226Propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

Product 1

HCID 46893803(7-{5-[(2,6-dichlorophenoxy)methyl]-1H-1,2,3-triazol-1-yl}-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetic acid

Procedure

The title compound was prepared using analogous procedures described in EXAMPLE 3 from propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate and 2,6-dichlorophenyl prop-2-yn-1-yl ether. 1H NMR (400 MHz, DMSO-d6): δ 12.14 (s, 1 H), 7.91 (s, 1 H), 7.54 (d, 2 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 7.25 (t, 1 H), 7.11-7.00 (m, 2 H), 5.48-5.32 (m, 3 H), 4.78 (dd, 1 H), 4.37 (t, 1 H), 3.62 (d, 2 H), 3.43-3.34 (m, 1 H), 3.24-3.09 (m, 1 H), 3.09-2.97 (m, 1 H). MS (+ESI) m/z: 471.1.

Sources & evidence

ORD record
ord-620f3cd074a141e2b2c3622c2e30dd7a
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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