2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 68298741, compound

HRID 2271959Notes

Reaction equation

HRID 2271959 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C:18]1[CH:19]=[N:20][N:21]([CH:23]2[CH2:28][CH2:27][CH2:26][N:25]([CH3:29])[CH2:24]2)[CH:22]=1.[Cl:30][C:31]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]>>[Cl:30][C:31]1[CH:36]=[C:35]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[NH:17][C:18]2[CH:19]=[N:20][N:21]([CH:23]3[CH2:28][CH2:27][CH2:26][N:25]([CH3:29])[CH2:24]3)[CH:22]=2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]

Participants

3

Reactant 2

HCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 68092005HCID 68092005, compound

Product 1

HCID 68298741HCID 68298741, compoundYield 74%

Procedure

Following general procedure F, {6-Bromo-4-[1-(1-methylpiperidin-3-yl)-1H-pyrazol-4-ylamino]quinolin-3-yl}(cyclopropyl)methanone (58 mg, 0.120 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (49 mg, 0.180 mmol) to afford the desired product (46 mg, 74%) as a yellow-green solid: 1H NMR (500 MHz, DMSO-d6) δ 10.86 (s, 1H), 9.08 (s, 1H), 8.24 (d, J=2.1 Hz, 1H), 8.04 (dd, J=8.8, 2.1 Hz, 1H), 7.93-7.83 (m, 2H), 7.43 (s, 1H), 7.39-7.30 (m, 2H), 4.19-4.12 (m, 1H), 2.95-2.81 (m, 3H), 2.29-2.15 (s, 5H), 2.01-1.89 (m, 4H), 1.02-0.92 (m, 4H).; ESI MS m/z 520 [C28H27ClFN5O2+H]+; HPLC 98.6% (AUC), tR=10.16 min.

Sources & evidence

ORD record
ord-be020e0cd1f44b4daa788eb8b04672a1
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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