2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66716276, compound

HRID 2271847Notes

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:14])[CH3:13])=[C:5]2[NH:15][C:16]1[CH:17]=[N:18][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:20][CH:21]=1.[Cl:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[C:32]([F:45])[C:31]=1[OH:46]>>[Cl:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)[CH:33]=[C:32]([F:45])[C:31]=1[OH:46]

Participants

Reactant 2

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

HCID 86692873HCID 86692873, compound

Product 1

HCID 66716276HCID 66716276, compoundYield 31.5%

Procedure

Following general procedure D, [1-(6-bromo-4-(6-(4-methylpiperazin-1-yl)pyridin-3-ylamino)quinolin-3-yl)ethanone (50 mg, 0.113 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (34 mg, 0.124 mmol) to afford the desired product (18 mg, 31%) as a yellow-orange solid: 1H NMR (500 MHz, CD3OD) δ 9.08 (s, 1H), 8.07 (d, J=3 Hz, 1H), 7.91 (s, 2H), 7.82 (s, 1H), 7.49 (dd, J=12, 2.0 Hz, 1H), 7.00-6.92 (m, 3H), 3.66 (t, J=10 Hz, 4H), 2.77 (s, 3H), 2.62 (t, J=10 Hz, 4H), 2.39 (s, 3H); ESI MS m/z 506, [C27H25ClFN5O2+H]+; HPLC 98.9% (AUC), tR=14.39 min.

Sources & evidence

ORD record: ord-4cdcadd99d0146e5be658caadb7d81c0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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