Sodium Carbonate → N-(2-chloro-5-(2-(isopropylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

HRID 2077604Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:20]=[CH:19][C:11]2[N:12]=[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])[S:14][C:10]=2[CH:9]=1.[Cl:21][C:22]1[C:27]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[Cl:21][C:22]1[C:27]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:26][C:25]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)=[CH:24][N:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A reaction tube was charged with Pd(Ph3P)4 (13.6 mg, 11.8 μmol), 2.0 M aqueous sodium carbonate (235 μl, 471 μmol), 6-bromo-N-isopropylbenzo[d]thiazol-2-amine (63.9 mg, 235 μmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (100 mg, 235 μmol) and 0.9 mL EtOH. The tube was sealed and the mixture was heated at 80° C. for 3 h. The mixture was concentrated and the crude material was purified by silica gel chromatography 0-10% MeOH/CH2Cl2 and reverse phase chromatography to provide N-(2-chloro-5-(2-(isopropylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (26 mg, 23%) as an off-white solid. MS (ESI pos. ion) m/z calc'd for C22H21ClN4O3S2: 489.0/491.0. found 488.9/491.0.

Workup

customThe tube was sealed
concentrationThe mixture was concentrated
customthe crude material was purified by silica gel chromatography 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-fb47b2af01664ddfbb2dbc8f50caa982
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928140B2

Reaction notes

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