Toluene → HCID 59370337, compound

HRID 1848570Notes

Reaction equation

HRID 1848570 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:26]=[CH:25][C:12]([C:13]([N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH3:16])=[O:14])=[CH:11][C:10]=1B1OC(C)(C)C(C)(C)O1.Br[C:37]1[CH:38]=[CH:39][C:40]([Cl:43])=[N:41][CH:42]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:8][C:9]1[CH:26]=[CH:25][C:12]([C:13]([N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH3:16])=[O:14])=[CH:11][C:10]=1[C:37]1[CH:42]=[N:41][C:40]([Cl:43])=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27344145-Bromo-2-chloropyridineHCID 686026284-chloro-N-(2-methoxy-phenyl)-N-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

Product 1

HCID 59370337HCID 59370337, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of toluene (1.5 mL) and water (0.5 mL) containing 4-chloro-N-(2-methoxy-phenyl)-N-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (60 mg, 0.15 mmol), 5-bromo-2-chloro-pyridine (29 mg, 0.15 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol), Na2CO3 (2N, 0.15 mL, 0.3 mmol), was bubbled with N2 for 5 min, then heated at 100° C. for 12 hrs. The mixture was filtered and purified by prep. LCMS to yield 4-chloro-3-(6-chloro-pyridin-3-yl)-N-(2-methoxy-phenyl)-N-methyl-benzamide 2-1 (22.6 mg). MS: 386.7 (M+H)+; tR=7.77 min (method 2).

Workup

  1. customwas bubbled with N2 for 5 min
  2. filtrationThe mixture was filtered
  3. custompurified by prep

Sources & evidence

ORD record
ord-8557919e6f2c496b8b27dbd360611905
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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