HCID 66715437, compound → HCID 66715790, compound

HRID 2271848Notes

Reaction equation

HRID 2271848 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:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=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][C:11]=2[F:12])[N:8]=[CH:7][C:6]([C:13]([CH:15]2[CH2:16][CH2:17]2)=[O:14])=[C:5]3[NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][N:26]([CH3:27])[CH3:28])=[CH:23][CH:24]=2)[CH:33]=[C:32]([F:45])[C:31]=1[OH:46]

Participants

3

Reactant 2

HCID 66715437HCID 66715437, compoundHCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 66715790HCID 66715790, compoundYield 24.1%

Procedure

Following general procedure D, ((6-bromo-4-(4-((dimethylamino)methyl)phenylamino)-7-fluoroquinolin-3-yl)(cyclopropyl)methanone (40 mg, 0.090 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (31 mg, 0.113 mmol) to afford the desired product (11 mg, 24%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 10.70 (s, 1H), 9.06 (s, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.75 (d, J=12 Hz, 1H), 7.26 (d, J=8.5 Hz, 2H), 7.21 (d, J=6.5 Hz, 2H), 7.09 (d, J=8.5, 2H), 3.40 (s, 2H), 2.77 (quint, J=15 Hz, 1H), 2.13 (s, 6H), 0.86 (m, 4H); ESI MS m/z 508, [C28H24ClF2N3O2+H]+; HPLC 98.7% (AUC), tR=10.83 min.

Sources & evidence

ORD record
ord-cd1b77f2cae94796b51ce4bb8db09432
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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