Potassium Carbonate → Methyl 6-benzothiazol-2-yl-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

HRID 2251600Notes

Reaction equation

HRID 2251600 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+].Br[C:51]1[S:52][C:53]2[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=2[N:55]=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>[S:52]1[C:53]2[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=2[N:55]=[C:51]1[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:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:7][C:6]=2[CH:22]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 6120402-Bromo-1,3-benzothiazoleHCID 2733548Bis(pinacolato)diboraneHCID 59642990Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

Product 1

HCID 59643042Methyl 6-benzothiazol-2-yl-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst2×

Procedure

Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate (600 mg, 1.459 mmol, 1 eq.), Pd(PPh3)4 (85 mg, 0.073 mmol, 0.05 eq.), bis(pinacolato)diboron (480 mg, 1.9 mmol, 1.3 eq.) and KOAc (216 mg, 2.2 mmol, 1.5 eq.), then Pd(PPh3)4 (85 mg, 0.073 mmol, 0.05 eq.), 2-bromo-1,3-benzothiazole (375 mg, 1.75 mmol, 1.2 eq.) and K2CO3 (1 g, 7.3 mmol, 5 eq.) were used according to GP6 to yield the title product as a colorless solid.

Sources & evidence

ORD record
ord-9a80f53b951e4b3d87b54d64789a7b81
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

Loading…