N-bromobutanimide → HCID 53354697, compound
Reaction equation
[OH:1][CH2:2][C@@:3]([C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]2[N:18]=[CH:17][C:16]3[CH:19]=[CH:20][N:21]([CH2:22][CH3:23])[C:15]=3[CH:14]=2)=[O:11])=[CH:8][CH:7]=1)([OH:5])[CH3:4].[Br:26]N1C(=O)CCC1=O>ClCCl>[Br:26][C:19]1[C:16]2[CH:17]=[N:18][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:24]=[CH:25][C:6]([C@:3]([OH:5])([CH3:4])[CH2:2][OH:1])=[CH:7][CH:8]=3)=[CH:14][C:15]=2[N:21]([CH2:22][CH3:23])[CH:20]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 50 mL pear flask was added (R)-4-(1,2-dihydroxypropan-2-yl)-N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)benzamide (13, 125 mg, 0.368 mmol) in dichloromethane (3.7 ml). At 0° C., 1-bromopyrrolidine-2,5-dione (66 mg, 0.37 mmol) was added to the mixture, and the mixture was kept in the refrigerator over the weekend. After concentration in vacuo, the crude product was purified by preparatory HPLC (TFA mode, 15-65% ACN/water). Combined fractions were neutralized by NaHCO3, concentrated and extracted into EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated. The residue was then re-suspended in ACN and water, and then freeze dried to give the desired product (R)—N-(3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(1,2-dihydroxypropan-2-yl)benzamide (20, 10 mg, 7%) as a light orange powder. 1H NMR (DMSO-d6) δ 10.62 (s, 1H), 8.50 (s, 1H), 8.36 (s, 1H), 7.97-8.05 (m, 2H), 7.70 (s, 1H), 7.54-7.61 (m, 2H), 5.00 (s, 1H), 4.71 (t, J=5.8 Hz, 1H), 4.21 (d, J=7.1 Hz, 2H), 3.46 (dd, J=5.8, 2.3 Hz, 2H), 1.42 (s, 4H), 1.39 (t, J=7.2 Hz, 3H); ESI-MS: m/z 418 (M+H)+.