Potassium Carbonate → HCID 58993588, compound

HRID 391449Notes

Reaction equation

HRID 391449 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:16][O:17][CH2:18][C:19]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH:7]=1.[CH3:38]B1OB(C)OB(C)O1.O1CCOCC1.O.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([CH3:38])[CH:3]=[C:4]([CH2:16][O:17][CH2:18][C:19]3([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:23][CH2:24]3)[CH:5]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 218864351,4-Dioxane--water (1/1)HCID 58993705HCID 58993705, compound

Product 1

HCID 58993588HCID 58993588, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
120 °C

Procedure

A microwave tube was charged with tert-butyl 4-(((5-bromo-4′-cyanobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (48 mg, 0.09 mmol), trimethyl boroxine (13 μL, 0.09 mmol), and tetrakis(triphenylphosphine) palladium(0) (10 mg, 9 μmol). The tube was flushed with nitrogen, treated with a mixture of 1,4-dioxane/water (9:1, 2 mL) and potassium carbonate (35.1 mg, 0.25 mmol). The tube was sealed and heated at 120° C. for 1 h via microwave. After cooling to room temperature, the reaction was concentrated and purified by preparative HPLC to give 11 mg (27%). LC/MS: tR=3.50 min, 497.33 (MH)+. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=4 min., Flow rate=4 mL/min.).

Workup

  1. customThe tube was flushed with nitrogen
  2. customThe tube was sealed
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction was concentrated
  5. custompurified by preparative HPLC
  6. customto give 11 mg (27%)

Sources & evidence

ORD record
ord-9cbb3ad7b7f04a91813c2911591e49c6
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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