Potassium Carbonate → HCID 16037477, compound

HRID 1806270Notes

Reaction equation

HRID 1806270 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[C:35]([CH2:39][NH:40][CH2:41][CH2:42][C:43]#[N:44])[CH:36]=[N:37][CH:38]=2)O1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>O.CO>[C:43]([CH2:42][CH2:41][NH:40][CH2:39][C:35]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:14]2[CH2:15][CH2:16][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:18][CH2:19]2)[CH:38]=[N:37][CH:36]=1)#[N:44]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 113844275-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideHCID 66723229HCID 66723229, compound

Product 1

HCID 16037477HCID 16037477, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (30 mg, 0.072 mmol) was added 3-({[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methyl}amino)propanenitrile (24.8 mg, 0.086 mmol). To this mixture was added dioxane (0.75 mL), followed by a solution of potassium carbonate (60 mg, 0.434 mmol) in water (0.25 mL) and SK-0002-A (4.4 mg, 0.007 mmol). The vials were capped and reacted in a CEM microwave at 150° C. for 30 min. The reaction was loaded onto a 2 g SCX SPE cartridge primed with 3 mL of methanol. The cartridge was then sequentially eluted with water (3 mL), methanol (9 mL), and 2M NH3 in MeOH (6 mL). The NH3 in MeOH fractions were dried under a stream of N2 at 40° C. The crude product was purified on the Agilent MDAP with UV (230 nm) and MS detection. The desired fractions were passed thru a 5 g CHQAX cartridge primed with 4 mL of methanol and 4 mL of water. The solvents were evaporated under a stream of N2 at 65° C. to give 6.2 mg of the title compound (17.4%).

Workup

  1. customThe vials were capped
  2. customreacted in a CEM microwave at 150° C. for 30 min
  3. washThe cartridge was then sequentially eluted with water (3 mL), methanol (9 mL), and 2M NH3 in MeOH (6 mL)
  4. dry with materialThe NH3 in MeOH fractions were dried under a stream of N2 at 40° C
  5. customThe crude product was purified on the Agilent MDAP with UV (230 nm) and MS detection
  6. customThe solvents were evaporated under a stream of N2 at 65° C.

Sources & evidence

ORD record
ord-93b7ba9634c44d5e970e1c78bdcd90e0
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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