2-Benzothiazolamine, 6-bromo- → 6-(4-(Benzyloxy)-3-fluorophenyl)benzo[d]thiazol-2-amine

HRID 1965843Notes

Reaction equation

HRID 1965843 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:20]1[CH:29]=[CH:28][C:23]2[N:24]=[C:25]([NH2:27])[S:26][C:22]=2[CH:21]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:20]2[CH:29]=[CH:28][C:23]3[N:24]=[C:25]([NH2:27])[S:26][C:22]=3[CH:21]=2)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 851492-Benzothiazolamine, 6-bromo-HCID 27377884-Benzyloxy-3-fluorophenylboronic Acid

Product 1

HCID 592830136-(4-(Benzyloxy)-3-fluorophenyl)benzo[d]thiazol-2-amine

Procedure

Compound 6-(4-(benzyloxy)-3-fluorophenyl)benzo[d]thiazol-2-amine (W146) was prepared using the general procedure for Suzuki coupling reaction between 4-(benzyloxy)-3-fluorophenylboronic acid (100 mg, 0.4 mmol) and 6-bromobenzo[d]thiazol-2-amine (92 mg, 0.4 mmol), as a white solid (65 mg, 58%). 1H NMR (400 MHz, acetone-d6) δ 7.92 (d, J=2.0 Hz, 1 H), 7.54-7.51 (m, 3 H), 7.49-7.46 (m, 1 H), 7.46-7.40 (m, 4 H), 7.37-7.33 (m, 1 H), 7.30-7.26 (m, 1 H), 6.86 (brs, 2 H), 5.25 (s, 2 H); MS (ESI) m/z 351 (M+H+).

Sources & evidence

ORD record
ord-ab737ae43b8a4104a9adea0a85353317
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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