Potassium Carbonate → HCID 89761707, compound

HRID 528556Notes

Reaction equation

HRID 528556 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][C:13]2[CH:17]=[C:18]([S:21]([N:24]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])[CH:19]=[CH:20][C:12]1=2.B1([C:48]2[CH2:53][CH2:52][N:51]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:50][CH:49]=2)OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.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>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:24]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[S:21]([C:18]2[CH:19]=[CH:20][C:12]3[N:11]([C:3]4[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=4[C:48]4[CH2:53][CH2:52][N:51]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:50][CH:49]=4)[CH2:16][CH2:15][O:14][C:13]=3[CH:17]=2)(=[O:23])=[O:22])=[CH:36][CH:35]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 89761660HCID 89761660, compound

Product 1

HCID 89761707HCID 89761707, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A microwave vial was charged with 4-(2-bromo-4-nitrophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.136 g, 0.220 mmol) (STEP 1, EXAMPLE 64), 3,6-dihydro-2h-pyridine-1-N-boc-4-boronic acid pinacol ester (0.136 g, 0.440 mmol), tetrakis(triphenylphosphine)palladium(0) (0.025 g, 0.022 mmol), and K2CO3 (0.152 g, 1.101 mmol). The solids were diluted with dioxane (1.468 mL) and water (0.734 mL), and the reaction was heated under microwave irradiation at 100° C. for 30 minutes. The reaction was diluted with water and DCM, the layers separated. The aqueous was washed once more with DCM, and the organics were combined and dried using a phase separator to yield material. After concentration under a vacuum, the material was taken up in methanol (and a small amount of DCM) and purified via 5 g SCX column to provide tert-butyl 4-(2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-5-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate, which was taken forward without further purification. m/z (ESI) 720.0 (M+H)+.

Workup

  1. customthe layers separated
  2. washThe aqueous was washed once more with DCM
  3. customdried
  4. customto yield material
  5. concentrationAfter concentration under a vacuum
  6. custompurified via 5 g SCX column

Sources & evidence

ORD record
ord-65a7c985b10f4b24a0c5def84d0b73d7
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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