Chloroform → HCID 59655772, compound

HRID 2054342Notes

Reaction equation

HRID 2054342 reaction equation
[C:1]1(=[O:29])[N:5]([CH2:6][CH:7]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][N:18]=3)[O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12.[CH:30]([Cl:33])(Cl)[Cl:31]>Cl.C1C=CC=CC=1>[Cl:31][C:21]1[CH:20]=[CH:19][N:18]=[C:17]2[C:22]=1[CH:23]=[C:15]([CH:7]([OH:8])[CH2:6][N:5]1[C:4](=[O:24])[C:3]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]3[C:1]1=[O:29])[NH:16]2.[O:10]1[CH:9]=[CH:14][CH2:13][CH2:12][CH2:11]1.[Cl:33][C:30]1[CH:20]=[CH:19][N:18]=[C:17]2[C:22]=1[CH:23]=[C:15]([CH:7]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)[CH2:6][N:5]1[C:4](=[O:24])[C:3]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]3[C:1]1=[O:29])[NH:16]2

Participants

7

Reactant 2

HCID 6212ChloroformHCID 59655782HCID 59655782, compound

Product 3

HCID 80803,4-dihydro-2H-pyranHCID 59655772HCID 59655772, compoundYield 63%HCID 59655775HCID 59655775, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 313Hydrochloric AcidSolvent

Procedure

Following the same procedure as for 2-[2-Phthalimido-1-(2,3,5,6-tetrahydropyran-2-yl)oxyethyl]-7-azaindole, from 8c (1.3 g, 3.8 mmol) in CHCl3 (50 ml), 6N HCl in benzene (5 ml) and 2,3-dihydropyrane (1.7 ml, 19 mmol), 4-chloro-2-[2-phthalimido-1-(2,3,5,6-tetrahydropyran-2-yl)oxyethyl]-7-azaindole (1.0 g, 63%) as a diastereomeric mixture (1:1) was obtained.

Sources & evidence

ORD record
ord-912be7c518324f59bea3e4e995ef9408
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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