2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178484101, compound

HRID 2271782Notes

Reaction equation

HRID 2271782 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.[F: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]>>[CH:15]1([C:13]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([N:25]([CH3:26])[CH3:27])[CH2:21][CH2:20]2)=[CH:3][C:2]([C:33]2[CH:34]=[C:29]([F:28])[C:30]([OH:45])=[C:31]([F:44])[CH:32]=2)=[C:11]([F:12])[CH:10]=3)=[O:14])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 576554062,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178484099HCID 178484099, compound

Product 1

HCID 178484101HCID 178484101, compoundYield 29.2%

Procedure

Following general procedure F, {6-bromo-4-[trans-4-(dimethylamino)cyclohexylamino]-7-fluoroquinolin-3-yl}(cyclopropyl)methanone (43 mg, 0.099 mmol) was reacted with 2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (38 mg, 0.149 mmol) to afford the desired product (14 mg, 29%) as a light yellow solid: NMR (300 MHz, CD3OD) δ 9.27 (s, 1H), 8.37 (d, J=7.8 Hz, 1H), 7.68 (d, J=11.1 Hz, 1H), 7.33 (d, J=7.8 Hz, 2H), 4.31 (s, 1H), 3.47-3.35 (m, 1H), 3.27 (s, J=6.8 Hz, 1H), 2.88 (s, 5H), 2.87-2.75 (m, 1H), 2.43 (s, 2H), 2.26 (s, 2H), 1.88-1.64 (m, 4H), 1.35-1.13 (m, 4H), ESI MS m/z 484 [C27H28F3N3O2+H]+; HPLC 98.3% (AUC), tR=8.83 min.

Sources & evidence

ORD record
ord-14f88c3b1eee4618ba7871393a83c515
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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