2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178458761, compound

HRID 2271786Notes

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](=[O:15])[CH2:13][CH3:14])=[C:5]2[NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][N:24]([CH3:26])[CH3:25])[CH2:19][CH2:18]1.[Cl:27][C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[C:30]([F:43])[C:29]=1[OH:44]>>[Cl:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:15])[CH2:13][CH3:14])=[C:5]3[NH:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][N:24]([CH3:26])[CH3:25])[CH2:19][CH2:18]2)[CH:31]=[C:30]([F:43])[C:29]=1[OH:44]

Participants

Reactant 2

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

HCID 178458755HCID 178458755, compound

Product 1

HCID 178458761HCID 178458761, compoundYield 28.2%

Procedure

Following general procedure M, 1-(6-bromo-4-((trans-4-((dimethylamino)methyl)cyclohexyl)amino)quinolin-3-yl)propan-1-one (125 mg, 0.30 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (90 mg, 0.33 mmol) to afford the desired product (41 mg, 28%) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 10.46 (d, J=8.0 Hz, 1H), 8.96 (s, 1H), 8.33 (d, J=2.2 Hz, 1H), 8.04 (dd, J=8.7, 1.9 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.64-7.57 (m, 2H), 4.13-4.07 (m, 1H), 3.13 (q, J=7.2 Hz, 2H), 2.22-2.15 (m, 2H), 2.13 (s, 6H), 1.87 (d, J=12.9 Hz, 2H), 1.57-1.42 (m, 3H), 1.16-0.99 (m, 5H). ESI MS m/z 484 [C27H31ClFN3O2+H]+; HPLC 98.5% (AUC), tR=8.36 min.

Sources & evidence

ORD record: ord-12e7cbc4a93d46cca5000f196856d420
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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