Potassium Carbonate → HCID 118022079, compound

HRID 518554Notes

Reaction equation

HRID 518554 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:13])[C:5](=[O:12])[N:6]([CH:8]2[CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[F:14][C:15]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][C:19]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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]>[CH:8]1([N:6]2[C:5](=[O:12])[C:4]([CH3:13])=[CH:3][C:2]([C:23]3[CH:22]=[C:21]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])[CH:20]=[CH:19][C:18]=3[O:17][C:16]3[CH:38]=[CH:39][C:40]([F:42])=[CH:41][C:15]=3[F:14])=[CH:7]2)[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 118021895HCID 118021895, compoundHCID 131732855HCID 131732855, compound

Product 1

HCID 118022079HCID 118022079, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound of Example 483, step 3 (27 mg, 0.11 mmol), N-[4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide (55 mg, 0.13 mmol), K2CO3 (46 mg, 0.33 mmol) and Pd(dppf)2Cl2 (8 mg, 0.011 mmol) in DMF (2 mL) were reacted and purified in a manner similar to Example 483, step 4 to give the title compound (16 mg, 32%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.65 (s, 1H), 7.42 (s, 1H), 7.26-7.27 (m, 1H), 7.13 (dd, J=8.8, 2.8 Hz, 1H), 6.97-6.89 (m, 2H), 6.83 (d, J=9.2 Hz, 2H), 6.54 (s, 1H), 5.09-5.18 (m, 1H), 3.04 (s, 3H), 2.53-2.46 (m, 2H), 2.23-2.18 (m, 2H), 2.16 (s, 3H), 1.87-1.81 (m, 2H). LCMS: 461 (M+H)+

Workup

  1. custompurified in a manner similar to Example 483, step 4

Sources & evidence

ORD record
ord-229053fa637a45e3bf91874d94b69294
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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