2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178484100, compound

HRID 2271783Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:13]([CH:15]1[CH2:17][CH2:16]1)=[O:14])=[C:5]2[NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([N:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([F:44])[C:30]=1[OH:45]>>[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[F:12])[N:8]=[CH:7][C:6]([C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])=[C:5]3[NH:18][C@H:19]2[CH2:20][CH2:21][C@H:22]([N:25]([CH3:27])[CH3:26])[CH2:23][CH2:24]2)[CH:32]=[C:31]([F:44])[C:30]=1[OH:45]

Participants

Reactant 2

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

HCID 178484099HCID 178484099, compound

Product 1

HCID 178484100HCID 178484100, compoundYield 90%

Procedure

Following general procedure F, {6-bromo-4-[trans-4-(dimethylamino)cyclohexylamino]-7-fluoroquinolin-3-yl}(cyclopropyl)methanone (38 mg, 0.087 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (35 mg, 0.131 mmol) to afford the desired product (39 mg, 90%) as a green solid: 1H NMR (300 MHz, CD3OD) δ 9.19 (s, 1H), 8.29 (d, J=8.1 Hz, 1H), 7.60 (d, J=11.8 Hz, 1H), 7.49 (s, 1H), 7.42 (dt, J=11.6, 2.0 Hz, 1H), 4.18 (s, 1H), 2.86 (s, 6H), 2.85-2.78 (m, 1H), 2.42 (s, 2H), 2.19 (s, 2H), 1.76-1.62 (m, 4H), 1.22-1.07 (m, 5H); ESI MS m/z 500 [C27H28ClF2N3O2+H]+; HPLC 97.4% (AUC), tR=9.21 min.

Sources & evidence

ORD record: ord-8a3e074802d941b2a7cdf1fbb158c709
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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