4-Fluorobenzyl chloride → {(R)-7-[5-(4-Fluoro-benzyl)-[1,2,3]triazol-1-yl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}-acetic acid

HRID 570667Notes

Reaction equation

HRID 570667 reaction equation
[C:1]1([C:7]2([C:12]3[N:16]([CH:17]4[CH2:33][N:21]5[C:22]6[C:27]([C:28]([CH2:29][C:30]([OH:32])=[O:31])=[C:20]5[CH2:19][CH2:18]4)=[CH:26][CH:25]=[CH:24][CH:23]=6)[N:15]=[N:14][CH:13]=3)CCCC2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:34]C1C=CC(CC#C)=CC=1.FC1C=CC(CCl)=CC=1.C([Si](C)(C)C)#C.[N-]=[N+]=[N-]>>[F:34][C:4]1[CH:5]=[CH:6][C:1]([CH2:7][C:12]2[N:16]([C@H:17]3[CH2:33][N:21]4[C:22]5[C:27]([C:28]([CH2:29][C:30]([OH:32])=[O:31])=[C:20]4[CH2:19][CH2:18]3)=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:15]=[N:14][CH:13]=2)=[CH:2][CH:3]=1

Participants

6

Reactant 5

HCID 96024-Fluorobenzyl chlorideHCID 33558AzideHCID 66111TrimethylsilylacetyleneHCID 105586681-Fluoro-4-prop-2-ynyl-benzeneHCID 46893926{7-[5-(1-Phenyl-cyclopentyl)-[1,2,3]triazol-1-yl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}-acetic acid

Product 1

HCID 46892777{(R)-7-[5-(4-Fluoro-benzyl)-[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 enantiomerically pure propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate from EXAMPLE 6 and 1-fluoro-4-prop-2-yn-1-ylbenzene prepared from 4-fluorobenzyl chloride and ethynyltrimethylsilane described in EXAMPLE 8 EXAMPLE 28.1 and 28.2 were prepared from the chiral azide with the retention time of 10.3 and 11.5 min respectively from EXAMPLE 6. MS (+ESI) m/z: 405.1.

Sources & evidence

ORD record
ord-79d4eb822e3946d893efa2353767396e
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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