2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178519802, compound

HRID 2271817Notes

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@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][N:25]2[CH2:29][CH2:28][C@@H:27]([F:30])[CH2:26]2)[CH2:20][CH2:19]1.[Cl:31][C:32]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[C:34]([F:47])[C:33]=1[OH:48]>>[Cl:31][C:32]1[CH:37]=[C:36]([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[CH2:15][CH2:16]2)=[O:13])=[C:5]3[NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([CH2:24][N:25]3[CH2:29][CH2:28][C@@H:27]([F:30])[CH2:26]3)[CH2:20][CH2:19]2)[CH:35]=[C:34]([F:47])[C:33]=1[OH:48]

Participants

Reactant 2

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

HCID 178519793HCID 178519793, compound

Product 1

HCID 178519802HCID 178519802, compoundYield 63%

Procedure

Following general procedure D, (6-bromo-4-((trans-4-(((R)-3-fluoropyrrolidin-1-yl)methyl)cyclohexyl)amino)quinolin-3-yl)(cyclopropyl)methanone (47 mg, 0.10 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (43 mg, 0.16 mmol) to afford the desired product (33.9 mg, 63%) as a yellow solid. 1H NMR (500 MHz, CDCl3) 1H NMR (500 MHz, CDCl3) δ 10.78 (br s, 1H), 9.24 (s, 1H), 8.24 (d, J=2.1 Hz, 1H), 8.03 (d, J=8.7 Hz, 1H), 7.84 (dd, J=8.7, 2.1 Hz, 1H), 7.44-7.39 (d, J=2.0 Hz, 1H), 7.29 (dd, J=11.1, 2.0 Hz, 1H), 5.25-5.10 (m, 1H), 4.10-4.04 (m, 1H), 2.91-2.65 (m, 4H), 2.51-2.27 (m, 5H), 2.24-2.01 (m, 5H), 1.65-1.50 (m, 3H), 1.31-1.21 (m, 1H), 1.13-1.04 (m, 4H). ESI MS m/z 540 [C30H32ClF2N3O2+H]+; HPLC>99% (AUC), tR=10.95 min.

Sources & evidence

ORD record: ord-622b1438527b4e60bf8a35131a1c8cf9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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