1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one → US10023592, Example 118

HRID 518334Notes

Reaction equation

HRID 518334 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].[CH3:21][N:22]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:24][C:23]1=[O:37]>O1CCOCC1.C(=O)(O)[O-].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:3][C:2]=1[C:26]1[CH:25]=[CH:24][C:23](=[O:37])[N:22]([CH3:21])[CH:27]=1

Participants

6

Reactant 2

HCID 454801941-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 617127003-Bromo-4-(2,4-difluorophenoxy)benzenesulfonamide

Product 1

HCID 118022583US10023592, Example 118Yield 18%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 769Bicarbonate IonSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-4-(2,4-difluorophenoxyl)benzenesulfonamide (1 eq., 62 mg), the title compound of Example 98, step 1 (40 mg, 0.17 mmol), Pd(dppf)Cl2 (10 mg, 8%) in 1,4-dioxane (880 μL) and saturated bicarbonate solution (aq) (220 μL) were reacted at 105° C. for 30 min in a manner similar to Example 117. Work up and preparative HPLC, also in a similar manner, gave the title compound (12 mg, 18%) as a white solid. 1H NMR (DMSO, 400 MHz): δ3.51 (s, 3H), 6.49 (d, J=9.4, 1H), 4.15 (q, J=6.9, 2H), 6.45 (d, J=9.4 Hz, 1H), 7.20-7.23 (m, 3H), 7.64 (dd, J=2.6, 9.4 Hz, 1H), 7.72-7.74 (m, 2H), 7.89 (d, J=2.6 Hz, 1H). LCMS (M+H)+=393.

Sources & evidence

ORD record
ord-de7f24a3c509489db19bd0928c7078f5
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

Loading…