Potassium Phosphate, Tribasic → HCID 86692999, compound

HRID 2173131Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:19]3[C:20](=[O:23])[O:21][CH2:22][C:18]=3[C:17]=2I)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([CH:40]2[CH2:45][CH2:44]CCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:19]3[C:20](=[O:23])[O:21][CH2:22][C:18]=3[C:17]=2[CH:44]2[CH2:45][CH2:40]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a microwave tube charged with tert-butyl-4-[2-(4-iodo-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate (100 mg, 0.21 mmol) and a stir bar was added palladium acetate (3.6 mg, 0.016 mmol), tricyclohexylphosphine (8.9 mg, 0.032 mmol), cyclopropyl boronic acid (27 mg, 0.32 mmol), and potassium phosphate (160 mg, 0.74 mmol). The tube was sealed, and injected toluene (2 mL) and water (100 uL). The mixture was purged three times with nitrogen, and heated to 100° C. for 30 minutes. LC showed formation of the desired product. The reaction was purified by silica gel chromatography to afford tert-butyl-4-[2-(4-cyclopropyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate. LC-MS (IE, m/z): 387 [M+1]+.

Workup

customThe tube was sealed
customThe mixture was purged three times with nitrogen
customThe reaction was purified by silica gel chromatography

Sources & evidence

ORD record: ord-41cac634a4804f57a9f943f9b6a16381
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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