Cesium carbonate → 5-(Cyclohexylmethyl)-4-(3,5-di-tert-butylphenyl)-1-methyl-1H-pyrrole-2-sulfonamide

HRID 1844740Notes

Reaction equation

[CH:1]1([CH2:7][C:8]2[N:12]([CH3:13])[C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([C:22]1[CH:23]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=1)([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]1([CH2:7][C:8]2[N:12]([CH3:13])[C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[C:24]2[CH:23]=[C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of compound 25e (67.1 mg, 200 μmol), 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72.8 mg, 230 μmol), Cs2CO3 (326 mg, 1.0 mmol) and Pd(dppf)Cl2 (22 mg) in dioxane and water was heated at 110° C. under microwave irradiation for 1 h. The solvent was removed and purified by prep-TLC to afford compound 25 (35 mg, 40%) as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 7.43 (t, J=1.5 Hz, 1H), 7.24 (s, 1H), 7.08 (d, J=1.5 Hz, 1H), 4.68 (s, 2H), 3.44 (s, 3H), 2.49 (d, J=7.8 Hz, 2H), 1.55-1.41 (m, 6H), 1.34 (s, 18H), 1.00-0.98 (m, 3H), 0.69-0.65 (m, 2H). MS Calcd.: 444.3; MS Found: 445.3 (M+1).

Workup

customThe solvent was removed
custompurified by prep-TLC

Sources & evidence

ORD record: ord-154330de5a84499db7b07c3769685a86
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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