2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715741, compound

HRID 2271963Notes

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:23]=[CH:22][C:21]([CH:24]([OH:29])[CH2:25][N:26]([CH3:28])[CH3:27])=[CH:20][CH:19]=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]=[CH:20][C:21]([CH:24]([OH:29])[CH2:25][N:26]([CH3:28])[CH3:27])=[CH:22][CH:23]=2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]

Participants

Reactant 2

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

HCID 86692894HCID 86692894, compound

Product 1

HCID 66715741HCID 66715741, compoundYield 40.2%

Procedure

Following general procedure A-1, {6-bromo-4-[4-(2-(dimethylamino)-1-hydroxyethyl)phenylamino]quinolin-3-yl}(cyclopropyl)methanone (50 mg, 0.110 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (30 mg, 0.165 mmol) to afford the desired product (23 mg, 40%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) 9.41 (s, 1H), 8.22 (dd, J=8.8, 2.0 Hz, 1H), 8.02 (d, J=8.8 Hz, 2H), 7.66 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.23 (s, 1H), 7.09-7.02 (m, 1H), 5.20 (dd, J=10.6, 3.8 Hz, 1H), 3.31-3.20 (m, 2H), 3.03 (s, 3H), 2.97 (s, 3H), 2.89-2.80 (m, 1H), 1.25-1.14 (m, 4H); ESI MS m/z 520 [C29H27ClFN3O3+H]+; HPLC 94.8% (AUC), tR=11.31 min.

Sources & evidence

ORD record: ord-0487aeed65bd48e495e86864f17ac955
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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