Benzothiazole → 5-Benzothiazol-2-yl-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 506628Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:12]=[C:13](I)[CH:14]=1)=[O:8])[CH3:5].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[S:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[N:44]=[CH:43]1>CN(C=O)C.[Cu]I.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:12]=[C:13]([C:43]2[S:42][C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]=2)[CH:14]=1)=[O:8])[CH3:5]

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of 5-iodo-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (150 mg, 0.37 mmol) in 1 ml dry DMF were added CuI (15.24 mg, 20% eq), Pd(OAc)2 (4.2 mg, 5% eq), PPh3 (19.5 mg, 20% eq) and benzothiazole (63.5 mg, 1.5 eq) at room temperature. The reaction mixture was heated to 150° C. by microwave irradiation for 45 minutes. The reaction mixture was cooled and extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by preparative HPLC to give 5-benzothiazol-2-yl-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (150 mg, 60%). MS (M+H)=417.

Workup

temperatureThe reaction mixture was cooled
extractionextracted with EtOAc
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-6aa5e42f927b427e91fcda7c1f2cf13a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786110B2

Reaction notes

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