4-Chloro-1-(4-fluoro-2-hydroxyphenyl)butan-1-one → HCID 69514301, compound

HRID 1764925Notes

Reaction equation

HRID 1764925 reaction equation
[CH2:1]1[N:11]2[C:12]3[C:8]([C@@H:9]4[CH2:16][NH:15][CH2:14][CH2:13][C@@H:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[O:3][CH2:2]1.Cl[CH2:18][CH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[OH:30])=[O:22]>>[CH2:1]1[N:11]2[C:12]3[C:8]([C@@H:9]4[CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=5[OH:30])=[O:22])[CH2:14][CH2:13][C@@H:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[O:3][CH2:2]1

Participants

3

Reactant 2

HCID 147738734-Chloro-1-(4-fluoro-2-hydroxyphenyl)butan-1-oneHCID 21302475HCID 21302475, compound

Product 1

HCID 69514301HCID 69514301, compound

Procedure

The title compound was prepared by the method of Example 361 as a yellow oil (8 mg, 17%) from (±)-cis-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole (30 mg, 0.12 mmol) and 4-chloro-1-(4-fluoro-2-hydroxyphenyl)-1-butanone (52 mg, 0.24 mmol). 1H NMR (CDCl3, 300 MHz) δ1.85-2.13 (m, 5H), 2.25-2.47 (m, 3H), 2.63-2.95 (m, 3H), 2.99 (t, J=7.0 Hz, 2H), 3.17-3.35 (m, 3H), 4.43 (dd, J=6.9, 2.2 Hz, 2H), 6.59-6.75 (m, 5H), 7.81 (dd, J=8.7, 6.6 Hz, 1H) ppm.

Sources & evidence

ORD record
ord-ddaf96180de04de18ea23d944d711c1c
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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