Potassium Carbonate → HCID 59643005, compound

HRID 2251601Notes

Reaction equation

HRID 2251601 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Cl.Br[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=1.C([O-])([O-])=O.[K+].[K+]>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>[C:16]1([C:8]2([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:7][C:6]3[CH:22]=[C:2]([C:56]4[CH:55]=[CH:54][N:53]=[CH:52][CH:57]=4)[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]=3[O:9]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 59642990Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylateHCID 713705042-Bromopyridine--hydrogen chloride (1/1)

Product 1

HCID 59643005HCID 59643005, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst2×

Procedure

Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate (400 mg, 0.973 mmol, 1 eq.), Pd(PPh3)4 (100 mg, 0.087 mmol, 0.09 eq.), bis(pinacolato)diboron (320 mg, 1.26 mmol, 1.3 eq.) and KOAc (150 mg, 1.5 mmol, 1.5 eq.), then Pd(PPh3)4 (112 mg, 0.097 mmol, 0.1 eq.), 2-bromo-pyridine hydrochloride (265 mg, 1.36 mmol, 1.4 eq.) and K2CO3 (680 mg, 4.9 mmol, 5 eq.) were used according to GP6 to yield the title product as a colorless solid.

Sources & evidence

ORD record
ord-ede8888fa88a430790cb1ddd4ce593eb
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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