2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178467123, compound

HRID 526147Notes

Reaction equation

HRID 526147 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1.[Cl:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[C:26]([F:39])[C:25]=1[OH:40]>>[ClH:1].[Cl:23][C:24]1[CH:29]=[C:28]([C:2]2[N:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]2)[CH:27]=[C:26]([F:39])[C:25]=1[OH:40]

Participants

3

Reactant 2

HCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178467151HCID 178467151, compound

Product 1

HCID 178467123HCID 178467123, compoundYield 57%

Procedure

Following general procedure II, 1-[6-chloro-4-(trans-4-hydroxycyclohexylamino)-1,5-naphthyridin-3-yl]ethanone (160 mg, 0.50 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (160 g, 0.60 mmol) followed by formation of the hydrochloride salt to afford the desired product (120 mg, 57%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.11 (s, 1H), 8.45 (d, J=9.1 Hz, 1H), 8.30 (d, J=9.0 Hz, 1H), 8.11 (s, 2H), 5.60 (dq, J=10.1, 4.5 Hz, 1H), 4.94-4.83 (m, 1H), 3.75 (tt, J=7.6, 3.9 Hz, 1H), 3.66 (s, 2H), 3.41-3.31 (m, 1H), 2.75 (s, 3H), 2.38 (dd, J=9.0, 5.3 Hz, 2H), 2.14-2.07 (m, 2H), 2.03 (s, 1H), 1.74-1.57 (m, 4H); ESI MS m/z 446 [M+H]+; HPLC 96.7% (AUC), tR=11.1 min.

Sources & evidence

ORD record
ord-14d423e421f541b390e4525f5911f05a
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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