Potassium Carbonate → HCID 86631023, compound

HRID 1806257Notes

Reaction equation

HRID 1806257 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:30]([NH2:32])=[O:31])[CH:17]=[C:18](B4OC(C)(C)C(C)(C)O4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].Br[C:34]1[N:35]=[C:36]([CH2:39][NH:40][CH2:41][C:42]([F:45])([F:44])[F:43])[S:37][CH:38]=1.[C:46](=[O:49])([O-])[O-:47].[K+].[K+]>O1CCOCC1.O.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>[F:43][C:42]([F:45])([F:44])[C:46]([OH:47])=[O:49].[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:30]([NH2:32])=[O:31])[CH:17]=[C:18]([C:34]4[N:35]=[C:36]([CH2:39][NH:40][CH2:41][C:42]([F:44])([F:45])[F:43])[S:37][CH:38]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 598289293-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamideHCID 66722761HCID 66722761, compound

Product 1

HCID 86631023HCID 86631023, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (46 mg, 0.1 mmol) in dioxane (2 mL) and water (0.7 mL) was added N-[(4-bromo-1,3-thiazol-2-yl)methyl]-2,2,2-trifluoroethanamine (30 mg, 0.11 mmol) and potassium carbonate (83 mg, 0.6 mmol). The resulting mixture was degassed for 5 min before the addition of tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.01 mmol). The mixture was reacted in a CEM microwave tube at 160° C. for 20 min. Organic layers were separated and concentrated. The resulting residue was purified by Gilson Preparatory HPLC to give 25 mg of the title compound (47.2%).

Workup

  1. customThe mixture was reacted in a CEM microwave tube at 160° C. for 20 min
  2. customOrganic layers were separated
  3. concentrationconcentrated
  4. customThe resulting residue was purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-10346cde84c840db81972376955d1256
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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