2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 136266713, compound

HRID 526106Notes

Reaction equation

HRID 526106 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:22])[CH3:21])=[C:13]3[NH:23][C:24]2[CH:25]=[N:26][C:27]([NH:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:28][CH:29]=2)[CH:5]=[C:6](Cl)[C:7]=1[OH:8].[Cl:36]C1C=C(B2OC(C)(C)C(C)(C)O2)C=C([F:52])C=1O>>[ClH:1].[ClH:36].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:22])[CH3:21])=[C:13]3[NH:23][C:24]2[CH:25]=[N:26][C:27]([NH:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:28][CH:29]=2)[CH:5]=[C:6]([F:52])[C:7]=1[OH:8]

Participants

3

Reactant 2

HCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 136266716HCID 136266716, compound

Product 1

HCID 136266713HCID 136266713, compoundYield 195.8%

Procedure

Following general procedure II, 1-[6-(3,5-dichloro-4-hydroxyphenyl)-4-{6-[2-(dimethylamino)ethylamino]pyridin-3-ylamino}-1,5-naphthyridin-3-yl]ethanone (69 mg, 0.18 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (74 mg, 0.27 mmol) followed by formation of the trihydrochloride salt to afford the desired product (71 mg, 66%) as a yellow-orange solid: 1H NMR (500 MHz, CD3OD) δ 9.40 (s, 1H), 8.49 (d, J=9.0 Hz, 1H), 8.41 (d, J=9.1 Hz, 1H), 8.23 (d, J=2.5 Hz, 1H), 7.87 (dd, J=9.4, 2.5 Hz, 1H), 7.42 (br s, 2H), 7.06 (d, J=9.4 Hz, 1H), 3.91 (t, J=6.4 Hz, 2H), 3.47 (t, J=6.4 Hz, 2H), 2.99 (s, 6H), 2.85 (s, 3H); ESI MS m/z 495 [M+H]+; HPLC 98.9% (AUC), tR=8.97 min.

Sources & evidence

ORD record
ord-b5bc1674803a4130b5a9745d0f571c73
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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