2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 5-(1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1698101Notes

Reaction equation

HRID 1698101 reaction equation
BrC1S[C:4]2C=C(OC)C=C[C:5]=2N=1.BrC1C=CC(B2OC(C)(C)C(C)(C)O2)=CN=1.CO[C:31]1[CH:46]=[CH:45][C:34]2[N:35]=[C:36]([C:38]3[CH:39]=[N:40][C:41](N)=[N:42][CH:43]=3)[S:37][C:33]=2[CH:32]=1>>[S:37]1[C:33]2[CH:32]=[CH:31][CH:46]=[CH:45][C:34]=2[N:35]=[C:36]1[C:38]1[CH:4]=[CH:5][C:41]([NH:42][CH3:43])=[N:40][CH:39]=1

Participants

4

Reactant 3

HCID 27947152-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 112187652-Bromo-6-methoxy-1,3-benzothiazoleHCID 248040695-(6-Methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine

Product 1

HCID 248042395-(1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Procedure

2-Bromo-6-methoxy-1,3-benzothiazole (49 mg, 0.20 mmol) and 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (68 mg, 0.24 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine, with the following exceptions: The reaction was stirred for 2 h and was then allowed to reach rt on. The mixture was filtered through a plug of silica and Na2SO4, eluting with DCM. The volume of the filtrate was reduced in a centrifuge and the remainder was purified by HPLC to give the title compound (4.2 mg). 1H NMR (CHLOROFORM-d: CD3OD) δ 8.93 (d, 1H) 8.21 (dd, 1H) 7.92 (d, 1H) 7.68 (d, 1H) 7.43 (d, 1H) 7.12 (dd, 1H) 3.89 (s, 3H).

Workup

  1. customto reach rt
  2. filtrationThe mixture was filtered through a plug of silica and Na2SO4
  3. washeluting with DCM
  4. customthe remainder was purified by HPLC

Sources & evidence

ORD record
ord-9881137ef1934e8383029e444db23a7a
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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