5-Bromo-2-(methylthio)benzo[d]thiazole → 2-Benzyl-5-bromo-1,3-benzothiazole

HRID 1972986Notes

Reaction equation

HRID 1972986 reaction equation
[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15](C3C=C(C4CCNCC4)N4C=3C(N)=NC=N4)[CH:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:33]C1C=CC2SC(SC)=NC=2C=1.[Br-].C([Zn+])C1C=CC=CC=1>>[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([Br:33])=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 28012715-Bromo-2-(methylthio)benzo[d]thiazoleHCID 585293605-(2-Benzyl-1,3-benzothiazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amineHCID 178419772HCID 178419772, compound

Product 1

HCID 585293922-Benzyl-5-bromo-1,3-benzothiazoleYield 48%

Procedure

In a manner similar to the procedure described for Step 2 of the preparation of 5-(2-benzyl-1,3-benzothiazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and using 5-bromo-2-(methylthio)-1,3-benzothiazole and benzylzinc bromide as starting material, 1.30 g (48%) of the desired product was isolated. 1H NMR (400 MHz, DMSO-d6) δ 8.18 (s, 1H), 7.99 (d, 1H), 7.56 (d, 1H), 7.40-7.18 (m, 5H), 4.44 (s, 2H); LC-MS m/z [M+H]+304.3 & 306.3, RT 5.16 min.

Sources & evidence

ORD record
ord-400d9931751f4ecfb9c35f875b07f298
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…