(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate → HCID 86700279, compound

HRID 879467Notes

Reaction equation

HRID 879467 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1.[C:17]([O:21][C@@H:22]([C:28]1[C:43]([CH3:44])=[CH:42][C:31]2[N:32]=[C:33]([C:35]3[CH:40]=[CH:39][N:38]=[C:37](Cl)[CH:36]=3)[S:34][C:30]=2[C:29]=1[C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH3:20])([CH3:19])[CH3:18]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[OH-].[K+].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[C:17]([O:21][C@@H:22]([C:28]1[C:43]([CH3:44])=[CH:42][C:31]2[N:32]=[C:33]([C:35]3[CH:40]=[CH:39][N:38]=[C:37]([N:8]4[C:16]5[CH:15]=[CH:14][N:13]=[CH:12][C:11]=5[CH2:10][CH2:9]4)[CH:36]=3)[S:34][C:30]=2[C:29]=1[C:45]1[CH:46]=[CH:47][C:48]([Cl:51])=[CH:49][CH:50]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH3:18])([CH3:19])[CH3:20]

Participants

7

Reactant 2

HCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetateHCID 86700280HCID 86700280, compound

Product 1

HCID 86700279HCID 86700279, compound

Reagents, catalysts & solvents 4

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 14797Potassium HydroxideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

In a 5 mL microwave reaction tube, 2,3-dihydro-1H-pyrrolo[3,2-c]pyridine TFA salt (excess), (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (26 mg, 0.05 mmol), bis(tri-tert-butylphosphine)palladium(0) (4 mg, 15%), cetyltrimethylammonium bromide (3 mg) were charged with 1 mL toluene, then 1 drop of 50% KOH aqueous solution was added. The reaction was heated to 105° C. for 1 hour. LC-MS of the reaction crude show desired product. The reaction crude was extracted using ethyl acetate form brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C34H34ClN4O3S: 613.1 (M+H+); Found: 613.3 (M+H+).

Sources & evidence

ORD record
ord-b3676024e66049f8a5930535ffa3277c
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…