2-(Methylamino)ethanol → 2-(4-(2-((3-Fluoropropyl)(methyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol

HRID 717511Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C4CCCCO4)[CH:19]=3)=[C:16]([CH3:31])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:32]C4CCCCO4)[CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.[CH3:39][NH:40][CH2:41][CH2:42][OH:43].[F:44][CH2:45][CH2:46][CH2:47]I>>[F:44][CH2:45][CH2:46][CH2:47][N:40]([CH3:39])[CH2:41][CH2:42][O:43][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)=[C:16]([CH3:31])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:32])[CH:14]=3)[O:9]2)=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 80162-(Methylamino)ethanol

HCID 128991281-Iodo-3-fluoropropane

HCID 866828852-(4-iodophenyl)-4-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2H-chromene

Product 1

HCID 896203022-(4-(2-((3-Fluoropropyl)(methyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol

Procedure

The title compound was synthesized as described in general procedures F, I and J (z=1) using Intermediate 3 and 2-(methylamino)ethanol in general procedure F, and 1-fluoro-3-iodopropane in general procedure I. 1H NMR (400 MHz, DMSO-d6): δ 9.44 (s, 1H), 8.95 (s, 1H), 7.19 (d, 2H), 7.13 (t, 1H), 6.79 (d, 2H), 6.75-6.72 (m, 1H), 6.68 (d, 1H), 6.67-6.62 (m, 1H), 6.62-6.60 (m, 1H), 6.48 (s, 2H), 5.84 (s, 1H), 4.50 (t, 1H), 4.38 (t, 1H), 3.95 (t, 2H), 2.65 (t, 2H), 2.44 (t, 2H), 2.19 (s, 3H), 2.03 (s, 3H), 1.81-1.72 (m, 1H), 1.72-1.69 (m, 1H). LCMS: 464.2 (M+H)+.

Sources & evidence

ORD record: ord-fb17523c434948368f9ee4c6d04da472
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193714B2

Reaction notes

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