Tetramethyltin → HCID 136191347, compound

HRID 1793748Notes

Reaction equation

Br[C:2]1[C:10]2[N:9]=[C:8]([C:11]3[C:12](=[O:28])[NH:13][CH:14]=[CH:15][C:16]=3[NH:17][CH2:18][C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[OH:20])[NH:7][C:6]=2[CH:5]=[C:4]([CH2:29][N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)[CH:3]=1.[CH3:37][Sn](C)(C)C.[F-].[K+]>CN(C=O)C>[Cl:27][C:23]1[CH:22]=[C:21]([C@H:19]([OH:20])[CH2:18][NH:17][C:16]2[CH:15]=[CH:14][NH:13][C:12](=[O:28])[C:11]=2[C:8]2[NH:7][C:6]3[CH:5]=[C:4]([CH2:29][N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:3]=[C:2]([CH3:37])[C:10]=3[N:9]=2)[CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Through a mixture of (S)-3-[4-Bromo-6-(4-methyl-piperazin-1-ylmethyl)-1H-benzimidazol-2-yl]-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-1H-pyridin-2-one (80 mg, 0.14 mmol), tetramethyl tin (2.5 mL, excess), PdCl2 (PPh3)4 (10 mg, 0.014 mmol), and KF (40 mg, 0.7 mmol) in DMF (2 mL) in a vial was bubbled nitrogen, sealed, and heated to 100° C. for two days. The reaction mixture was passed through a small pad of celite. After concentration, the residue was purified by prep. HPLC to give the titled compound (34 mg, 48%). 1H NMR (400 MHz, CD3OD) δ 7.53 (1H, s), 7.45 (1H, s), 7.24–7.40 (4H, m), 7.09 (1H, s), 6.22 (1H, d, J=7.6 Hz), 4.99 (1H, t, J=6.4 Hz), 4.04 (2H, br s), 3.61–3.74 (2H, m), 2.98–3.34 (8H, m), 2.80 (3H, s), 2.58 (3H, s). LCMS (M+H)+ m/z 507 (t=1.29 min.).

Workup

customwas bubbled nitrogen
customsealed
concentrationAfter concentration
customthe residue was purified by prep

Sources & evidence

ORD record: ord-25e7603e3e8f415fab1e2c2360534542
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081454B2

Reaction notes

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