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 1944045Notes

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

Reactant 5

HCID 96024-Fluorobenzyl chloride

HCID 33558Azide

HCID 66111Trimethylsilylacetylene

HCID 105586681-Fluoro-4-prop-2-ynyl-benzene

HCID 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-a]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-ddb93b0176ed4aeb8b3f6a33c94267c6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394819B2

Reaction notes

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