7-Bromo-5-methylfuro[3,2-c]pyridin-4(5H)-one → US10023592, Example 378

HRID 575806Notes

Reaction equation

HRID 575806 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2B2OC(C)(C)C(C)(C)O2)[CH2:3][CH2:2]1.Br[C:26]1[C:27]2[O:36][CH:35]=[CH:34][C:28]=2[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=1.Br[C:38]1C2C(=CC=C(C(F)(F)F)C=2)C(=O)N(C)C=1>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:38])(=[O:13])=[O:14])=[CH:8][C:7]=2[C:26]2[C:27]3[O:36][CH:35]=[CH:34][C:28]=3[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 1180215737-Bromo-5-methylfuro[3,2-c]pyridin-4(5H)-oneHCID 1180220564-Bromo-2-methyl-6-(trifluoromethyl)isoquinolin-1-oneHCID 1234348592-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118022090US10023592, Example 378

Procedure

The title compound was prepared in a manner similar to Example 197, by substituting 2-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for 2-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 7-bromo-5-methylfuro[3,2-c]pyridin-4-one for 4-bromo-2-methyl-6-(trifluoromethyl)isoquinolin-1-one. 1H NMR (DMSO-d6, 400 MHz) δ 7.88 (m, 4H), 7.33 (d, J=9.4 Hz, 1H), 7.01 (d, J=2.0 Hz, 1H), 4.02 (d, J=6.8 Hz, 2H), 3.58 (s, 3H), 3.28 (m, 2H), 1.12 (t, J=7.4 Hz, 3H), 1.08 (m, 1H), 0.45 (m, 2H), 0.24 (m, 2H). LCMS: 388.1 (M+H)+

Sources & evidence

ORD record
ord-01a2cad44002447d81271b4e64cadc38
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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