Benzenamine, 4-bromo-N-methyl- → HCID 59282854, compound

HRID 1965845Notes

Reaction equation

HRID 1965845 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[CH:20][C:21]3[S:25][CH:24]=[N:23][C:22]=3[CH:26]=2)O1>>[S:25]1[C:21]2[CH:20]=[CH:19][C:18]([C:2]3[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=3)=[CH:26][C:22]=2[N:23]=[CH:24]1

Participants

3

Reactant 2

HCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 467390305-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazole

Product 1

HCID 59282854HCID 59282854, compound

Procedure

Compound 4-(benzo[d]thiazol-5-yl)-N-methylaniline (W189) was prepared using the general procedure for Suzuki coupling reaction between 4-bromo-N-methylaniline (56 mg, 0.3 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (78 mg, 0.3 mmol), as a white solid (20 mg, 28%). 1H NMR (400 MHz, acetone-d6) δ 9.22 (s, 1 H), 8.22 (d, J=1.6 Hz, 1 H), 8.08 (d, J=8.4 Hz, 1 H), 7.71 (dd, J=8.4, 1.6 Hz, 1 H), 7.56 (m, 2 H), 6.72 (m, 2 H), 5.14 (brs, 1 H), 2.83 (s, 0.5 H), 2.82 (s, 0.5 H); MS (ESI) m/z 241 (M+H+).

Sources & evidence

ORD record
ord-9df241e9bc0c462e9269ba79699dd4a5
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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