Potassium Phosphate, Tribasic → 4-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide

HRID 1178977Notes

Reaction equation

[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](I)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:31]1([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([S:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C:5]4[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=4)=[O:28])=[CH:10][CH:11]=3)(=[O:17])=[O:16])[CH:19]=2)[CH2:33][CH2:32]1

Participants

Conditions

Temperature: 100 °C

Procedure

Combine N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (0.50 g, 0.94 mmol), cyclopropylboronic acid (0.24 g, 2.8 mmol), tricyclohexylphosphine (0.05 g, 0.18 mmol), potassium phosphate (0.70 g, 3.30 mmol), and palladium acetate (0.02 g, 0.09 mmol) in a mixture of toluene (15 mL) and water (0.4 mL). Heat to 100° C. under nitrogen for 18 hours, filter through celite, and wash solids with EtOAc. Wash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4, and concentrate under vacuum. Purify by flash column on silica gel eluting with 0-50% EtOAc in hexanes to give the title compound (0.25 g, 60%). MS (ES) 449.2 (M+1)+, 447.4 (M−1)−.

Workup

filtrationfilter through celite
washwash solids with EtOAc
dry with materialWash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4
concentrationconcentrate under vacuum
customPurify by flash column on silica gel eluting with 0-50% EtOAc in hexanes

Sources & evidence

ORD record: ord-f07dbabf5c5547138b6ced4349f08f3a
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276516B2

Reaction notes

Loading…